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  • 51. Lake, F.
    et al.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Ti-mediated addition of diethylzinc to benzaldehyde. The effect of chiral additives2001In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 12, no 5, p. 755-760Article in journal (Refereed)
    Abstract [en]

    In the presence of a chiral tridentate bissulfonamide, the titanium-mediated addition of diethylzinc to benzaldehyde gave alkylated products ranging from the (R)-enantiomer, formed with an e.e. of 26%, to the (S)-enantiomer, formed in 72% e.e. The enantioselectivity was also affected by the presence of additional chiral mono- and bidentate ligands, with the reactions proceeding via complexes containing the chiral sulfonamide and the additive. The: addition of (1R,2R)-2,2-diphenyl-,12-ethanediamine and (1S,2S)-1.3-diphenyl-1,2-ethanediamine gave the (S)-product with e.e. of 49% and the (R)-product with 16% e.e., respectively, whereas without additives the (R)-product was obtained in 26% e.e, In the presence of (1R,2R)-1,2-diphenyl-1,2-ethanediamine only (i.e. without the chiral sulfonamide), the (S)-product formed with a 3% e.e.

  • 52. Larhed, M.
    et al.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Hallberg, A.
    Microwave-accelerated homogeneous catalysis in organic chemistry2002In: Accounts of Chemical Research, ISSN 0001-4842, E-ISSN 1520-4898, Vol. 35, no 9, p. 717-727Article, review/survey (Refereed)
    Abstract [en]

    The efficiency of microwave flash heating in accelerating organic transformations (reaction times reduced from days and hours to minutes and seconds) has recently-been proven in several different fields of organic chemistry. This specific account mainly summarizes our own experiences in developing rapid, robust, and selective microwave-assisted transition metal-catalyzed homogeneous reactions. Applications include selective Heck couplings, cross-couplings, and asymmetric substitutions. The science of green chemistry was developed to meet the increasing demand for environmentally benign chemical processes. We believe the combination of metal catalysis and microwave heating will be of importance in the search for green laboratory-scale synthesis.

  • 53.
    Laurell, Anna
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Opposite Enantiomers from Minor Enantiomer Recycling and Dynamic Kinetic Resolution Using a Single Biocatalyst2011In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 20-21, p. 3980-3984Article in journal (Refereed)
    Abstract [en]

    A one-pot recycling procedure comprising Lewis acid catalyzed enantioselective addition of acetyl cyanide to (E)-2-butenal to give the O-acetylated cyanohydrin and enzyme-catalyzed conversion of the minor product enantiomer back to (E)-2-butenal provided essentially enantiopure (2R,3E)-2-acetoxy-3-pentenenitrile in close to quantitative yield. The opposite enantiomer was obtained, albeit in lower yield and with lower enantiomeric purity than that observed from the minor enantiomer recycling, by dynamic kinetic resolution consisting of reversible addition of HCN to the aldehyde coupled to enzyme-catalyzed acetylation of the cyanohydrin.

  • 54.
    Laurell Nash, Anna
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Hertzberg, Robin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Wen, Ye-Qian
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dahlgren, Björn
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dual Lewis Acid/Lewis Base Catalyzed Acylcyanation of Aldehydes: A Mechanistic Study2016In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 11, p. 3821-3829Article in journal (Refereed)
    Abstract [en]

    A mechanistic investigation, which included a Hammett correlation analysis, evaluation of the effect of variation of catalyst composition, and low-temperature NMR spectroscopy studies, of the Lewis acid-Lewis base catalyzed addition of acetyl cyanide to prochiral aldehydes provides support for a reaction route that involves Lewis base activation of the acyl cyanide with formation of a potent acylating agent and cyanide ion. The cyanide ion adds to the carbonyl group of the Lewis acid activated aldehyde. O-Acylation by the acylated Lewis base to form the final cyanohydrin ester occurs prior to decomplexation from titanium. For less reactive aldehydes, the addition of cyanide is the rate-determining step, whereas, for more reactive, electron-deficient aldehydes, cyanide addition is rapid and reversible and is followed by rate-limiting acylation. The resting state of the catalyst lies outside the catalytic cycle and is believed to be a monomeric titanium complex with two alcoholate ligands, which only slowly converts into the product.

  • 55.
    Laurell Nash, Anna
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Hertzberg, Robin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Wen, Ye-Qian
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dual Lewis Acid-Lewis Base Catalyzed Acetylcyanation  of Aldehydes: A Mechanistic StudyManuscript (preprint) (Other academic)
  • 56. Laurell Nash, Anna
    et al.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Minor enantiomer recycling - CO2 formation as the driving force2014In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 248Article in journal (Other academic)
  • 57.
    Laurell Nash, Anna
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Widyan, Khalid
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Recycling Powered by Release of Carbon Dioxide2014In: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 6, no 12, p. 3314-3317Article in journal (Refereed)
    Abstract [en]

    In a cyclic process, fed with external chemical energy generated by the transformation of a compound with high chemical potential to carbon dioxide, the undesired enantiomer from a catalytic asymmetric reaction is continuously recycled to starting reagent. This minor enantiomer recycling is characterized by gradually increasing yields and product enantiomeric ratios. The requirements for maintaining a cyclic procedure are discussed; the necessity of a coupled exergonic process is demonstrated experimentally.

  • 58.
    Lega, Matteo
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. KTH Sch Chem Sci & Engn, Dept Chem, SE-10044 Stockholm, Sweden..
    Figliolia, Rosario
    Univ Naples Federico II, Dipartimento Sci Chim, I-80126 Naples, Italy..
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. KTH Sch Chem Sci & Engn, Dept Chem, SE-10044 Stockholm, Sweden..
    Ruffo, Francesco
    Univ Naples Federico II, Dipartimento Sci Chim, I-80126 Naples, Italy..
    Erratum to: Expanding the scope of the elpaN-type library: glucose-derived bis(pyridine-2-carboxamide) ligands (elpaN-Py) for molybdenum-catalyzed asymmetric allylic alkylations2013In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, no 25, p. 5259-5259Article in journal (Refereed)
  • 59.
    Lega, Matteo
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Figliolia, Rosario
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ruffo, Francesco
    Expanding the scope of the elpaN-type library: glucose-derived bis(pyridine-2-carboxamide) ligands (elpaN-Py) for molybdenum-catalyzed asymmetric allylic alkylations2013In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, no 20, p. 4061-4065Article in journal (Refereed)
    Abstract [en]

    The elpaN-Py family of ligands, which represents a subset of the elpaN-type library based on a-glucose, is described. The ligands are structural analogs of the privileged bis(pyridine-2-carboxamides) derived from trans-1,2-diaminocyclohexane, and differ for the type of substitution in the coordinating functions present in positions 1 and 2. Their ability to induce high enantioselectivity in asymmetric allylic alkylations promoted by molybdenum under microwave irradiation has been successfully demonstrated, starting from both a linear (ee up to 99%) and a branched substrate (ee up to 96%). The multifunctional nature of the sugar scaffold was exploited for the preparation of a polar ligand, through deprotection of the hydroxyl groups in positions 3, 4 and 6. In this version, it was possible to verify the performance in catalysis in alternative solvents, such as ionic liquids and water.

  • 60.
    Li, Ende
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Zhou, Hui
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Östlund, Victor
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Hertzberg, Robin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Regio- and stereoselective synthesis of conjugated trienes from silaborated 1,3-enynes2016In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 40, no 7, p. 6340-6346Article in journal (Refereed)
    Abstract [en]

    Products obtained from palladium-catalyzed regioselective cis-addition of (chlorodimethylsilyl)pinacolborane to the alkyne bond of 1,4-disubstituted 1,3-enynes were subjected to Suzuki-Miyaura coupling with alkenyl iodides. Hiyama coupling of the resulting silanol-functionalized trienes provided tetrasubstituted conjugated trienes with different substitution patterns, whereas protiodesilylation with fluoride gave trisubstituted trienes. The methodology presented gives access to conjugated trienes with control of regio- and stereochemistry.

  • 61.
    Li, Fei
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Wingstrand, Erica
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Widyan, Khalid
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Chiral Lewis base catalyzed enantioselective acetylcyanation of α-oxo esters2009In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 23, p. 3917-3922Article in journal (Refereed)
    Abstract [en]

    Acetyl cyanide adds to alkyl benzoylformates and to 2-oxoalkanoates to yield enantioenriched acylated cyanohydrins in one step in the presence of a catalytic amount of a chiral base. The reaction is accelerated by Lewis acids and by the addition of a catalytic amount of methanol. Under optimized conditions, 94% of a 94:6 mixture of the O-acetylated and non-protected cyanohydrins was formed from, methyl benzoylformate in the presence of cinchonidine; from, this mixture the acylated compound with 66% ee was isolated in 77% yield. Ethyl pyruvate and ierf-butyl 2-oxobutanoate were more reactive, and essentially full conversion to the products with 69 and 82% ee, respectively, was achieved. The reaction proceeds by a non-selective addition of cyanide ion to give the non-protected cyanohydrin followed by a dynamic kinetic resolution to provide the enantioenriched acetylated product.

  • 62. Luken, Christian
    et al.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Silaborations of 1,3-enynes - Substrate controlled allene/1,3-diene selectively2008In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 10, no 12, p. 2505-2508Article in journal (Refereed)
    Abstract [en]

    Silaboration of 1,3-enynes catalyzed by group 10 metal complexes affords 1,3-dienes with vinylborane and vinylsilane functions or 1,2-dienes with allylborane and vinylsilane functions. The type of product formed is determined by the size of the alkyne substituent.

  • 63.
    Lundgren, Stina
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ihre, Henrik
    GE Healthcare, Uppsala.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Enantioselective Cyanation of Benzaldehyde: an Asymmetric Polymeric Catalyst in a Microreactor2008In: ARKIVOC, ISSN 1424-6376, Vol. 6, p. 73-80Article in journal (Refereed)
    Abstract [en]

    A chiral salen ligand containing a carboxylic acid group was attached to macroporous monosized polystyrene-divinylbenzene beads grafted with (4-hydroxybutyl) vinyl ether groups. A Ti(IV) complex of the beads was used for enantioselective cyanations of benzaldehyde using trimethylsilyl cyanide and acetyl cyanide as cyanide sources using both conventional batch techniques and a microreactor.

  • 64.
    Lundgren, Stina
    et al.
    KTH, Superseded Departments, Chemistry.
    Lutsenko, S.
    KTH, Superseded Departments, Chemistry.
    Jönsson, C.
    KTH, Superseded Departments, Chemistry.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Polymer-Supported Pyridine-Bis(oxazoline). Application to Ytterbium Catalyzed Silylcyanation of Benzaldehyde2003In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 5, no 20, p. 3663-3665Article in journal (Refereed)
    Abstract [en]

    Terminal acetylenes containing hydroxy and carboxylic acid groups were subjected to Sonogashira coupling with 4-bromo-2,6-bis[(R)-4-phenyloxazolin-2-yl]pyridine and the resulting pybox derivatives were immobilized on Tentagel resins. Ytterbium(ill) chloride complexes of the polymeric ligands catalyzed the addition of trimethylsilyl cyanide to benzaldehyde with 80-81% ee. The ligands were reused more than 30 times without any loss in selectivity or activity, and the metal complexes could be recovered and reused at least four times, although with slightly decreasing activity.

  • 65.
    Lundgren, Stina
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Russom, Aman
    KTH, School of Electrical Engineering (EES), Microsystem Technology (Changed name 20121201).
    Jönsson, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Stemme, Göran
    KTH, School of Electrical Engineering (EES), Microsystem Technology (Changed name 20121201).
    Haswell, Stephen J.
    Andersson, Helene
    KTH, School of Electrical Engineering (EES), Microsystem Technology (Changed name 20121201).
    Moberg, Christina
    KTH, School of Electrical Engineering (EES), Microsystem Technology (Changed name 20121201).
    Micro reactors for the optimisation of reaction conditions in asymmetric metal catalysis2005In: Micro Total Analysis Systems 2004 / [ed] Laurell T; Nilsson J; Jensen K; Harrison DJ; Kutter JP, 2005, no 296, p. 445-447Conference paper (Refereed)
    Abstract [en]

    Two types of micro reactors were employed for enantioselective metal catalysed reactions. In the first type of reactor, an electroosmotic flow was used, whereas the second type of reactor used a pressure driven flow. The purpose of the study is to develop tools for rapid and efficient optimization of reactions, utilising minimum amounts of reagents.

  • 66.
    Lundgren, Stina
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Wingstrand, Erica
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Hamberg, Anders
    KTH, School of Biotechnology (BIO), Centres, Albanova VinnExcellence Center for Protein Technology, ProNova. KTH, School of Biotechnology (BIO), Biochemistry (closed 20130101).
    Hult, Karl
    KTH, School of Biotechnology (BIO), Centres, Albanova VinnExcellence Center for Protein Technology, ProNova. KTH, School of Biotechnology (BIO), Biochemistry (closed 20130101).
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    ORGN 402-Dual activation in enantioselective synthesis of cyanohydrins2006In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 232Article in journal (Other academic)
  • 67.
    Lundgren, Stina
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Wingstrand, Erica
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Lewis acid-Lewis base-catalysed enantioselective addition of alpha-ketonitriles to aldehydes2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, no 3, p. 364-372Article in journal (Refereed)
    Abstract [en]

    Additions of structurally diverse alpha-ketonitriles to aromatic and aliphatic prochiral aldehydes yielding highly enantioenriched acylated cyanohydrins were achieved using a combination of a titanium salen dimer and an achiral or chiral Lewis base. In most cases high yields and high enantioselectivities were observed. The ee was moderate in the initial part of the reaction but increased over time. This could be avoided, and higher ees obtained, by keeping the titanium complex, in the presence or absence of aldehyde and ketonitrile, at -40 degrees C prior to the addition of the Lewis base. A mechanism initiated by nucleophilic attack of the tertiary amine at the carbonyl carbon atom of the ketonitile is supported by C-13 labelling experiments.

  • 68.
    Lundgren, Stina
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Wingstrand, Erica
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Penhoat, Maël
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Dual Lewis Acid–Lewis Base Activation in Enantioselective Cyanation of Aldehydes Using Acetyl Cyanide and Cyanoformate as Cyanide Sources2005In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 127, no 33, p. 11592-11593Article in journal (Refereed)
  • 69. Lutsenko, S.
    et al.
    Jacobsson, U.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Preparation of L-threoninol and its bisoxazoline derivative2003In: Synthetic Communications, ISSN 0039-7911, E-ISSN 1532-2432, Vol. 33, no 4, p. 661-666Article in journal (Refereed)
    Abstract [en]

    (R,R)-Threoninol was prepared in one step from L-threonine in 86% isolated yield. The product was regioselectively transformed into 2,2-bis[(4R,5R)-4-(hydroxymethyl)-5-methyl-1,3-oxazolin-2-yl]propane in 42% isolated yield.

  • 70. Lutsenko, S.
    et al.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Microwave-mediated ruthenium-catalyzed asymmetric hydrogen transfer2001In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 12, no 18, p. 2529-2532Article in journal (Refereed)
    Abstract [en]

    Ru-catalyzed hydrogen transfer from propan-2-ol to acetophenone under microwave conditions using monotosylated (R,R)-diphenylethylenediamine as the chiral source afforded (R)-1-phenylethanol in >90% yield and 82% e.e. within 9 min, while use of ephedrine or norephedrine gave the same compound in high yield with 70 and 46% e.e., respectively. t-Butylphenylketone was reduced to (R)-2,2-dimethyl-1-phenyl-1-propanoI under the same conditions in close to quantitative yield, although with low enantioselectivity.

  • 71.
    Malkoch, Michael
    et al.
    KTH, Superseded Departments, Fibre and Polymer Technology.
    Hallman, Kristina
    KTH, Superseded Departments, Chemistry.
    Lutsenko, Serghey
    KTH, Superseded Departments, Chemistry.
    Hult, Anders
    KTH, Superseded Departments, Fibre and Polymer Technology.
    Malmström, Eva
    KTH, Superseded Departments, Fibre and Polymer Technology.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Dendritic oxazoline ligands in enantioselective palladium-catalyzed allylic alkylations2002In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 67, no 23, p. 8197-8202Article in journal (Refereed)
    Abstract [en]

    First to fourth generation dendritic substituents based on 2,2-bis(hydroxymethyl)propionic acid and (1R,2S,5R)-menthoxyacetic acid were attached to 2-(hydroxymethyl)pyridinooxazoline and his[4-(hydroxymethyl)oxazoline] compounds. The new ligands obtained were assessed in palladium-catalyzed allylic alkylations. The first type of ligands exhibited enantioselectivity similar to that of a benzoyl ester derivative, whereas the latter type of ligands afforded products with higher selectivity than the analogous benzoyl ester. The activity of the dendritic catalysts decreased with increasing generation.

  • 72.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Can C-3-symmetric receptors differentiate enantiomers?2006In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 45, no 29, p. 4721-4723Article in journal (Refereed)
  • 73.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Editorial: Chemistry in SwedenA Midsummer Night's Dream?2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 7, p. 1844-1845Article in journal (Other academic)
  • 74.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Mechanism of Diphenylprolinol Silyl Ether Catalyzed Michael Addition Revisited but Still Controversial2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 8, p. 2160-2162Article in journal (Other academic)
  • 75.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Minor enantiomer recycling - a strategy to improve enantioselectivity2016In: Pure and Applied Chemistry, ISSN 0033-4545, E-ISSN 1365-3075, Vol. 88, no 4, p. 309-316Article in journal (Refereed)
    Abstract [en]

    In enantioselective reactions, the major, desired enantiomer is commonly obtained along with the minor, undesired enantiomer. By continuous recycling of this undesired enantiomer back to starting material, products with improved enantiomeric purity can be obtained. Such in situ minor enantiomer recycling can be accomplished by coupling the catalytic reaction to an exergonic transformation of a sacrificial reagent. The method has been applied to the synthesis of O-acylated cyanohydrins, which serve as starting materials for a variety of biologically active compounds.

  • 76.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Molybdenum-Catalyzed and Tungsten-Catalyzed Enantioselective Allylic Substitutions2012In: Topics in Organometallic Chemistry / [ed] Kazmaier, U, Springer Berlin/Heidelberg, 2012, p. 209-234Chapter in book (Other academic)
    Abstract [en]

    Asymmetric allylic substitutions catalyzed by molybdenum and tungsten complexes provide branched chiral products from unsymmetrically substituted allylic reagents. Highly selective chiral ligands are available for both types of reactions, but for the tungsten-catalyzed substitutions, enantioselective reactions are only possible starting from achiral linear allylic substrates. A variety of stabilized carbanions can be used as nucleophiles. The molybdenum-catalyzed reaction has been applied to the synthesis of several biologically active compounds.

  • 77.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Recycling in Asymmetric Catalysis2016In: ACCOUNTS OF CHEMICAL RESEARCH, ISSN 0001-4842, Vol. 49, no 12, p. 2736-2745Article, review/survey (Refereed)
    Abstract [en]

    CONSPECTUS: Cyclic reaction networks consisting of an enantioselective product forming step and a reverse reaction of the undesired enantiomer back to starting reactant are important for the generation of compounds with high enantiomeric purity. In order to avoid an equilibrium racemic state, a unidirectional cyclic process where product formation and regeneration of starting reactant proceed through different mechanistic pathways is required. Such processes must necessarily include a thermodynamically unfavorable step, since the product of the forward reaction is the reactant of the reverse reaction and vice versa. Thermodynamically uphill processes are ubiquitous to the function of living systems. Such systems gain the required energy by coupling to thermodynamically downhill reactions. In the same way, artificial cyclic reaction networks can be realized in systems open to mass or energy flow, and an out-of equilibrium nonracemic steady state can be maintained as long as the system is supplied with energy. In contrast to a kinetic resolution, a recycling process where the minor enantiomer is converted to starting reactant can result in a quantitative yield, but the enantiomeric purity of the product is limited by the selectivity of the catalysts used for the reactions. On the other hand, in a kinetic resolution, the slowly reacting enantiomer can always be obtained in an enantiomerically pure state, although the yield will suffer. In cyclic reaction systems which use chiral catalysts for both the forward and the reverse processes, a reinforcing effect results, and selectivities higher than those achieved by a single chiral catalyst are observed. A dynamic kinetic resolution can in principle also lead to a quantitative yield, but lacks the reinforcing effect of two chiral catalysts. Most examples of cyclic reaction networks reported in the literature are deracemizations of racemic mixtures, which proceed via oxidation of one enantiomer followed by reduction to the opposite enantiomer. We have developed cyclic reaction networks comprising a carbon carbon bond formation. In these processes, the product is generated by the addition of a cyanide reagent to a prochiral aldehyde. This is followed by hydrolysis of the minor enantiomer of the product to generate the starting aldehyde. A unidirectional cycle is maintained by coupling to the exergonic transformation of the high potential cyanide reagent to a low potential compound, either a carboxylate or carbon dioxide. The products, which are obtained with high enantiomeric purity, serve as valuable starting materials for a variety of biologically and pharmaceutically active compounds.

  • 78.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Stereomutation in Trigonal-Bipyramidal Systems: A Unified Picture2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 44, p. 10290-10292Article in journal (Other academic)
    Abstract [en]

    Same difference: Berry pseutorotation (BPR) and Ugi turnstile rotation, which are generally treated as two distinctly different mechanisms for rearrangement of trigonal-bipyramidal structures, have been shown to be equivalent. Alternative mechanisms consist of sequences of pseudorotations proceeding in a single step.

  • 79.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    The Role of Symmetry in Asymmetric Catalysis2012In: Israel Journal of Chemistry, ISSN 0021-2148, Vol. 52, no 7, p. 653-662Article, review/survey (Refereed)
    Abstract [en]

    Chiral ligands and metal complexes with rotational (Cn, Dn) symmetry often have beneficial properties in asymmetric catalysis. The enhanced enantioselectivity frequently observed is a result of a reduction of competing reaction routes. This may be due to rotational symmetry in the catalyst, leading to a limited number of different catalyst-substrate interactions, or to formation of a limited number of catalytic species as a result of rotational symmetry in the ligand. The effect of symmetry is usually difficult to evaluate, since a change in symmetry properties necessarily is accompanied by structural modifications. In each situation the number of intermediate complexes, their electronic and steric properties, and their energy need to be analyzed. Although other factors may be more important than symmetry for achieving high enantioselectivity, a vast number of C2- and to some extent C3-symmetric ligands have been found to have excellent properties in asymmetric catalysis, providing products with high enantiomeric purity. Besides the benefit of symmetry in the ligand and catalyst, the symmetry of the substrate may be important since a gain in enantioselectivity can result from simultaneous asymmetric transformations of homotopic functional groups.

  • 80.
    Moberg, Christina
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Adolfsson, Hans
    Concepts in Asymmetric Catalysis2012In: Israel Journal of Chemistry, ISSN 0021-2148, Vol. 52, no 7, p. 571-571Article in journal (Other academic)
  • 81.
    Moberg, Christina
    et al.
    KTH, Superseded Departments, Chemistry.
    Belda, O.
    Frölander, Anders
    KTH, Superseded Departments, Chemistry.
    Lundgren, S.
    Zalubovskis, Raivis
    KTH, Superseded Departments, Chemistry.
    Enantio- and regioselectivity in Palladium- and Molybdenum-Catalyzed Allylic Alkylations2004In: Latvian Journal of Chemistry, ISSN 0868-8249, p. 131-138Article in journal (Refereed)
  • 82.
    Moberg, Christina
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Frölander, Anders
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    ORGN 31-Secondary interaction in hydroxy-containing phosphinooxazolines2007In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 234, p. 31-ORGN-Article in journal (Other academic)
    Abstract [en]

    Phosphinooxazolines, first employed by Williams, Pfaltz, and Helmchen, serve as versatile ligands for a variety of asym. catalytic reactions.  The hydroxy group in hydroxy-contg. phosphinooxazolines such as 1 can take part in hydrogen bonding to low valent metal ions, thereby affecting the conformation and, as a result, the stereochem. of catalytic reactions.  The hydroxy group is also capable of coordinating to high valent metal ions via the oxygen atom, resulting in more rigid complexes.  This leads for example to enhanced enantioselectivity in Rh- and Ir-catalyzed hydrosilylations of prochiral ketones.  The influence of these secondary interaction on the conformation and dynamics of metal complexes and on the selectivity in catalytic reactions will be discussed.

  • 83.
    Moberg, Christina
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Wingstrand, Erica
    Enantioenriched Acylated Cyanohydrins: Synthesis and Analysis2010In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, no 3, p. 355-367Article in journal (Refereed)
    Abstract [en]

    The addition of acyl cyanides to prochiral aldehydes catalyzed by a chiral Lewis acid and an achiral Lewis base produces highly enantioenriched O-acylated cyanohydrins. alpha-Keto esters undergo the same type of addition, although via a different mechanism in which the enantioselectivity originates from a chiral Lewis base. In the presence of a biocatalyst, the minor, undesired enantiomer obtained in the reactions with aldehydes can be selectively hydrolyzed to re-form the starting aldehyde, permitting the reaction to be run in a cyclic manner. The minor-enantiomer recycling results in an essentially enantiopure product. Selective enzymatic hydrolysis is also a key step in high-throughput analysis of conversions and enantiomeric ratios.

  • 84.
    Moberg, Christina
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Wingstrand, Erica
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    fei, Li
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Lundgren, Stina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Penhoat, Maël
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Enantioenriched cyanohydrins: Versatile insecticide intermediates2008In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 236, p. 95-AGRO-Article in journal (Other academic)
    Abstract [en]

    Several pyrethroid insecticides contain cyanoester functions.  Many of these are today used in racemic form or, in case they contain more than a single stereocenter, even as a mixt. of several stereoisomers, although it is known that both aquatic toxicity and biodegrdn. may differ for the two enantiomers.  We have obtained enantioenriched O-acylated cyanohydrins by the addn. of ketonitriles to prochiral aldehydes catalyzed by a chiral Lewis acid and an achiral Lewis base.  By this procedure, (S)-O-acetyl 2-hydroxy-3-butenenitrile was prepd. from acrolein and acetyl cyanide in 67% yield and 73% ee.  This product can be used as an intermediate in the synthesis of glufosinate, (S)-2-amino-4-[hydroxy(methyl)phosphinoyl]butyric acid.

  • 85.
    Moberg, Christina
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Wingstrand, Erica
    Lundgren, Stina
    Hamberg, Anders
    Penhoat, Mael
    Engstrom, Kann
    Hult, Karl
    KTH, School of Biotechnology (BIO), Biochemistry.
    ORGN 512-Asymmetric cyano-acylation of aldehydes: Use of a new high throughput screen for readout of conversion and ee2008In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 236, p. 512-ORGNArticle in journal (Refereed)
  • 86.
    Paavola, Sari
    et al.
    KTH, Superseded Departments, Chemistry.
    Zetterberg, Krister
    KTH, Superseded Departments, Chemistry.
    Privalov, Timofei
    KTH, Superseded Departments, Chemistry.
    Csoregh, I.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Aerobic oxidation of 1-phenylethanol catalyzed by palladaheterocycles2004In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 346, no 2-3, p. 237-244Article in journal (Refereed)
    Abstract [en]

    Cyclometallated palladium compounds with pyridine were shown to serve as more efficient catalysts for the aerobic oxidation of 1-phenylethanol than a previously investigated analogue with an oxazoline ring. Substituents with different electronic properties in the phenyl ring were shown to exhibit an only minor influence on the reactivity of the catalytic system. The first step in the reaction consists of the splitting of the acetate bridge in the dimeric starting complex and coordination of a ligand to palladium. By ab initio calculations it was shown that, in the presence of solvent, a complex with pyridine was more stable than that with the alcohol, whereas the opposite situation was found in the gas phase. The complex with coordinated alcohol was stabilized by hydrogen bonding. Good agreement was found between the computed structure and the X-ray structure of the initial palladaheterocycle 1.

  • 87. Pei, Y. X.
    et al.
    Brade, K.
    Brule, E.
    Hagberg, L.
    Lake, F.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    A general method for the preparation of chiral TREN derivatives2005In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 13, p. 2835-2840Article in journal (Refereed)
    Abstract [en]

    A general procedure for the preparation of C-3-symmetric TREN derivatives with backbone chirality has been developed. Stereo- and regioselective ring opening by ammonia of (S)-N-tosyl-2-isopropylaziridine, obtained starting from either the corresponding amino alcohol or amino acid, followed by deprotection of the amino groups afforded the parent chiral TREN compound in high overall yield. In addition to TREN compounds with primary amino groups, the synthetic method employed provides easy access to a variety of N,N',N-substituted derivatives. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

  • 88. Pei, Y. X.
    et al.
    Brule, E.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Modular multidentate phosphine ligands: application to palladium-catalyzed allylic alkylations2006In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 4, no 3, p. 544-550Article in journal (Refereed)
    Abstract [en]

    Multidentate phosphines were readily obtained by reaction of chiral multidentate amines, prepared via ring opening of (S)-N-tosyl-2-isopropylaziridine with ammonia, primary, and secondary amines, with achiral phosphorus containing building blocks. The phosphines were used in palladium-catalyzed alkylation of rac-3-cyclohexenyl and cyclopentenyl carbonates. The enantioselectivity and reactivity were largely dependent on the structure of the amine core of the ligands. Up to 88% ee was observed in reactions with the six-membered substrate.

  • 89.
    Pei, Yuxin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Brulé, Emilie
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    New multidendate phosphine ligands and their application in palladium-catalyzed asymmetric allylic alkylation2005In: ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY: Volume 230, 2005, p. U3420-U3421Conference paper (Other academic)
  • 90.
    Privalov, Timofei
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Linde, C.
    Zetterberg, K.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Theoretical studies of the mechanism of aerobic alcohol oxidation with palladium catalyst systems2005In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 24, no 5, p. 885-893Article in journal (Refereed)
    Abstract [en]

    Density functional theory (DFT) was applied to a comprehensive mechanistic study of the Pd(II)-catalyzed oxidation of alcohols by molecular oxygen. Both parts of the catalytic cycle, i.e., the oxidative dehydrogenation of the substrate and the regeneration of the catalyst by the co-oxidant, molecular oxygen, were studied. The catalytic cycle under consideration consists of intramolecular deprotonation, beta-hydride elimination, and migratory insertion steps, and it is relevant for a wide class of catalytic systems. In particular, a Pd(II) cyclometalated system was addressed and qualitatively compared with the Uemura system (Pd(OAc)(2)/pyridine) and with the Pd-carbene system. Geometries of the intermediate complexes and relative Gibbs free energies were identified along the proposed reaction path with the help of computational methods. The transition state for the beta-hydride elimination, which is the highest point on the energy profile of the catalytic cycle, was identified.

  • 91. Rahm, F.
    et al.
    Fischer, Andreas
    KTH, Superseded Departments, Chemistry.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Pyridyl phosphinites and pyridyl phosphites from chiral pyridyl alcohols - A modular approach2003In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 21, p. 4205-4215Article in journal (Refereed)
    Abstract [en]

    Chiral arylated pyridyl alcohols, pyridyl phosphinites and pyridyl phosphites were prepared by Suzuki arylation and/or O-functionalization with a chlorodiarylphosphane or a chloro-diarylphosphite of chiral 2-bromo-6-(1-hydroxyalkyl)pyridines or 2-(1-hydroxyalkyl) pyridines, with the chirality originating from the chiral pool. The pyridyl alcohols were assessed as catalysts for the addition of diethylzinc to benzaldehyde and the P,N-ligands were employed in the palladium-catalysed substitutions of rac-1,3-diphenyl-2-propenyl acetate and rac-2-cyclohexenyl acetate with dimethyl malonate. Moderate enantioselectivities were observed in the catalytic reactions. We observed kinetic resolution of the racemic acetate when using one of the phosphite ligands. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

  • 92. Rahm, F.
    et al.
    Stranne, R.
    Bremberg, U.
    Nordstrom, K.
    Cernerud, M.
    Macedo, E.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Preparation of chiral enantiopure 2-(hydroxyalkyl)pyridine derivatives. Use of the chiral pool2000In: Journal of the Chemical Society-Perkin Transactions 1, ISSN 1470-4358, no 12, p. 1983-1990Article, review/survey (Refereed)
    Abstract [en]

    Enantiomerically pure 2-(1-hydroxyalkyl)pyridines were prepared via reaction of 2-lithiopyridine with (R)-2,3-O-isopropylideneglyceraldehyde, methyl (S)-2-methoxypropionate and methyl (S)-2-methoxy-2-phenylacetate, obtained from D-mannitol, L-lactic acid and L-mandelic acid, respectively. 6,6'-Bis(1-hydroxyalkyl)-2,2'-bipyridines were obtained from the same naturally occurring chiral compounds and 2-bromo-6-lithiopyridine with subsequent Ni-catalysed coupling.

  • 93. Rahm, Fredrik
    et al.
    Fischer, Andreas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Inorganic Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Pyridyl phosphinites and pyridyl phosphites from chiral pyridyl alcohols - A modular approach (pg 4205, 2003)2008In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 10, p. 1817-1817Article in journal (Refereed)
  • 94. Stranne, R.
    et al.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Pyrrolidinopyridines in palladium-catalyzed allylic substitutions - Conformation of the ligand2001In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 11, p. 2191-2195Article in journal (Refereed)
    Abstract [en]

    The (R,R)-2-[(2,5-dimethylpyrrolidin-1-yl)methyl]pyridines 4, 5, and 6 carrying a 2-hydroxyalkyl, 2-alkoxyalkyl or 2-siloxyalkyl substituent in the 6-position of the pyridine ring were prepared and assessed in palladium-catalyzed allylations of 1,3-diphenylpropenyl acetate with malonate. All ligands having g-substituents with an S absolute configuration afforded the product with an R configuration in 80-84% ee, whereas those having substituents with an R absolute configuration gave the opposite product with a selectivity depending on the nature of the substituent (8-74% ee). It is believed that the enantioselectivity is dependent on the conformation of that substituent.

  • 95. Stranne, R.
    et al.
    Vasse, J. L.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Synthesis and application of chiral P,N-ligands with pseudo-meso and pseudo-C-2 symmetry2001In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 3, no 16, p. 2525-2528Article in journal (Refereed)
    Abstract [en]

    [GRAPHICS] Two diastereoisomeric P,N-ligands, (S,S)-1 and (R,S)-1, were synthesized and assessed in palladium-catalyzed allylic alkylations. With rac-1,3-diphenylpropenyl acetate as substrate, ligand (AS)-1, with pseudo-C-2 symmetry, exhibited higher reactivity and higher enantioselectivity than the pseudo-meso ligand (R,S)-1, whereas reversal reactivity and selectivity were observed with rac-3-cyclohexenyl acetate.

  • 96.
    Theveau, Laure
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Bellini, Rosalba
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dydio, Pawel
    Szabo, Zoltan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    van der Werf, Angela
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. University of Amsterdam, Netherlands.
    Sander, Robin Afshin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Reek, Joost N. H.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Cofactor-Controlled Chirality of Tropoisomeric Ligand2016In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 35, no 11, p. 1956-1963Article in journal (Refereed)
    Abstract [en]

    A new tropos ligand with an integrated anion receptor receptor site has been prepared. Chiral carboxylate and phosphate anions that bind in the anion receptor unit proved capable of stabilizing chiral conformations of the achiral flexible bidentate biaryl phosphite ligand, as shown by variable temperature H-1 and P-31 NMR spectroscopical studies of palladium(0) olefin complexes. Palladium allyl complexes of the supramolecular ligand-chiral cofactor assemblies catalyzed asymmetric allylic substitutions of rac-(E)-1,3-diphenyl-2-propenyl carbonate and rac-3-cyclohexenyl carbonate with malonate and benzylamine as nucleophiles to provide nonracemic products. Although moderate enantioselectivities were observed, (ee:s up to 66%), the results confirm the ability of the anionic guests to affect the conformation of the ligand.

  • 97.
    Tilliet, Mélanie
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Frölander, Anders
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Levacher, Vincent
    UMR 6014 IRCOF, CNRS, Université et INSA de Rouen.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Convenient Preparation of Bifunctional Pybox Ligands2008In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 64, no 44, p. 10244-10249Article in journal (Refereed)
    Abstract [en]

     Starting from a common easily available pybox derivative, chiral ditopic ligands with pendant Lewis basic sites consisting of amine or phosphine oxide functions attached in the 4-positions of the oxazoline rings were prepared by simple synthetic procedures. From the same pybox derivative, a macrocyclic ligand containing a diaza-18-crown-6-ether ring linked via triazole groups was obtained employing 'click' chemistry.

  • 98.
    Tilliet, Mélanie
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Frölander, Anders
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Lundgren, Stina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Levacher, Vincent
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Evaluation of new pyridine-bis(oxazoline) ligands in asymmetric catalysisManuscript (Other academic)
  • 99.
    Tilliet, Mélanie
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Frölander, Anders
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Zetterberg, Krister
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Szabo, Zoltan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Influence of Ligand Secondary Interactions on Dynamic Processes in Alkene Ir ComplexesManuscript (Other academic)
  • 100.
    Tilliet, Mélanie
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Lundgren, Stina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Levacher, Vincent
    Laboratoire de Chimie Organique Fine et Hétérocyclique, UMR 6014, Université et INSA de Rouen.
    Polymer-Bound Pyridine-Bis(oxazoline). Preparation through Click Chemistry and Evaluation in Asymmetric Catalysis2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, no 13, p. 2079-2084Article in journal (Refereed)
    Abstract [en]

    A pyridine-bis(oxazoline) ligand was efficiently immobilized by copper(I)-catalyzed azide-alkyne cycloaddition onto a polystyrene resin. The so obtained click-pybox resin 1a was associated with various metal salts (YbCl3, LuCl3, CuOTf) and the resulting resin-bound catalysts were explored in ring-opening of cyclohexene oxide, silylcyanation of benzaldehyde and alkynylation of imines. These new polymer-supported catalysts exhibit good to excellent performances in terms of catalytic activity, enantioselectivity and recyclability.

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