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  • 1.
    Angelin, Marcus
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Discovery-Oriented Screening of Dynamic Systems: Combinatorial and Synthetic Applications2010Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis is divided into six parts, all centered around the development of dynamic (i.e., reversibly interacting) systems of molecules and their applications in dynamic combinatorial chemistry (DCC) and organic synthesis.

    Part one offers a general introduction, as well as a more detailed description of DCC, being the central concept of this thesis. Part two explores the potential of the nitroaldol reaction as a tool for constructing dynamic systems, employing benzaldehyde derivatives and nitroalkanes. This reaction is then applied in part three where a dynamic nitroaldol system is resolved by lipase-catalyzed transacylation, selecting two out of 16 components.

    In part four, reaction and crystallization driven DCC protocols are developed and demonstrated. The discovery of unexpected crystalline properties of certain pyridine β-nitroalcohols is used to resolve a dynamic system and further expanded into asynthetic procedure. Furthermore, a previously unexplored tandem nitroaldol-iminolactone rearrangement reaction between 2-cyanobenzaldehyde and primarynitroalkanes is used for the resolution of dynamic systems. It is also coupled with diastereoselective crystallization to demonstrate the possibility to combine several selection processes. The mechanism of this reaction is investigated and a synthetic protocol is developed for asymmetric synthesis of 3-substituted isoindolinones.

    Part five continues the exploration of tandem reactions by combining dynamic hemithioacetal or cyanohydrin formation with intramolecular cyclization to synthesize a wide range of 3-functionalized phthalides.

    Finally, part six deals with the construction of a laboratory experiment to facilitate the introduction of DCC in undergraduate chemistry education. The experiment is based on previous work in our group and features an acetylcholinesterase-catalyzed resolution of a dynamic transthioacylation system.

  • 2.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Fischer, Andreas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Crystallization-induced secondary selection from a tandem driven dynamic combinatorial resolution process2008In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 73, no 9, p. 3593-3595Article in journal (Refereed)
    Abstract [en]

    Crystallization-induced secondary selection from a tandem driven dynamic combinatorial library is presented. In a one-pot experiment, an initial nitroaldol equilibrium was kinetically driven by a tandem reaction resulting in a subsequent dynamic library of diastereoisomers. This library was then further driven by a phase change, resulting in amplification and isolation of a highly diastereomerically enriched and synthetically interesting isoindolinone.

  • 3.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Larsson, Rikard
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Introducing Dynamic Combinatorial Chemistry: Probing the Substrate Selectivity of Acetylcholinesterase2010In: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328, Vol. 87, no 11, p. 1248-1251Article in journal (Refereed)
  • 4.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Larsson, Rikard
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Sakulsombat, Morakot
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dynamic combinatorial resolution2009In: Dynamic Combinatorial Chemistry: In Drug Discovery, Bioorganic Chemistry, and Materials Science / [ed] Miller, B., John Wiley & Sons, 2009, p. 169-200Chapter in book (Refereed)
  • 5.
    Angelin, Marcus
    et al.
    KTH, School of Education and Communication in Engineering Science (ECE), Lärande.
    Rahm, M.
    Gabrielsson, Erik
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Gumaelius, Lena
    KTH, School of Education and Communication in Engineering Science (ECE), Lärande.
    Rocket scientist for a day: Investigating alternatives for chemical propulsion2012In: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328, Vol. 89, no 10, p. 1301-1304Article in journal (Refereed)
    Abstract [en]

    This laboratory experiment introduces rocket science from a chemistry perspective. The focus is set on chemical propulsion, including its environmental impact and future development. By combining lecture-based teaching with practical, theoretical, and computational exercises, the students get to evaluate different propellant alternatives. To complete the task, they need to use several important curricular concepts, such as the breaking and formation of bonds, redox reactions, and thermodynamics. They also apply basic computational electronic structure calculations to investigate the energetic content of hitherto nonexisting alternatives. Finally, actual chemical rocket propulsion is demonstrated through the assembly and testing of a model rocket motor, employing a commercially available kit. The full experiment was developed for upper-level high school classes and is completed in a 3-h lab period. The experiment, or parts of it, has also been successfully used both in undergraduate programs and continuing education for teachers. 

  • 6.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Rahm, Martin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Fischer, Andreas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones: A Mechanistic Investigation2010In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, no 17, p. 5882-5887Article in journal (Refereed)
    Abstract [en]

    The mechanism of a base-catalyzed one-pot reaction of 2-cyanobenzaldehyde and primary nitroalkanes, to produce 3-substituted isoindolinones, has been investigated. A route starting with a nitroaldol (Henry) reaction, followed by a subsequent cyclization and rearrangement, was supported by intermediate analogue synthesis and DFT calculations. Direct diastereoselective crystallization from the reaction mixture was also achieved and studied for a number of substrates. Furthermore, the 3-substituted isoindolinones are an interesting group of compounds, both present important natural products, as well as being precursors to other valuable building blocks.

  • 7.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Making a Chemical Rainbow2010In: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328, Vol. 87, no 5, p. 504-506Article in journal (Refereed)
    Abstract [en]

    In this laboratory experiment, high school students are challenged to prepare a six-layered chemical "rainbow" in a test tube. Students start with six unknown, colorless liquids and six pigments ranging from violet to red. The experiment is problem based and forces the students to apply their knowledge of solubility and density and combine it with creative and critical thinking to come up with a successful strategy to make the rainbow. This is followed by experimental testing to find the unique solution. Finally, coloring and correct layering of the liquids produces the final and aesthetically pleasing result, a chemical rainbow.

  • 8.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Where's Ester? A Game That Seeks the Structures Hiding Behind the Trivial Names2010In: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328, Vol. 87, no 4, p. 406-407Article in journal (Refereed)
  • 9.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Fischer, Andreas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Crystallization Driven Asymmetric Synthesis of Pyridine β-Nitroalcoholsvia Discovery-Oriented Self-Resolution of a Dynamic System2010In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 33, p. 6315-6318Article in journal (Refereed)
    Abstract [en]

    The study of dynamic nitroaldol systems aided the discovery of a diastereoselective crystallization process through amplification of 2-nitro-1-(pyridine-4-yl)propan-1-ol. The phenomenon was further developed into an effective procedure for asymmetic synthesis of pyridine-nitroalcohols and several substrates were screened to this end. These results demonstrate how work with larger dynamic systems facilitates and increases the likelihood of serendipitous discoveries.

  • 10.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Fischer, Andreas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Tandem driven dynamic combinatorial resolution via Henry–iminolactone rearrangement2008In: ChemComm, ISSN 1359-7345, p. 768-770Article in journal (Refereed)
    Abstract [en]

    An unexplored type of tandem reaction is used to kinetically resolve a dynamic combinatorial library resulting in quantitative amplification of an interesting 3-substituted isoindolinone.

  • 11.
    Dong, Hai
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Pei, Zhichao
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Angelin, Marcus
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Byström, Styrbjörn
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Efficient Synthesis of β-D-Mannosides and β-D-Talosides by Double Parallel or Double Serial Inversion2007In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 72, no 10, p. 3694-3701Article in journal (Refereed)
    Abstract [en]

    A neighboring equatorial ester group plays a highly important role in the Lattrell-Dax (nitrite-mediated) carbohydrate epimerization reaction, inducing the formation of inversion compounds in good yields. On the basis of this effect, efficient synthetic routes to beta-D-mannosides and beta-D-talosides, from the corresponding beta-D-galactosides and beta-D-glucosides, have been designed. The present routes are based on multiple regioselective acylation via the respective stannylene intermediates, followed by inversions to the corresponding manno- and talopyranoside structures by nitrite or acetate substitution. It was found that the ester group was able to induce the inversion of its two neighboring groups in high yields following either a double parallel or a double serial inversion process. By combination of direct inversion, and neighboring- as well as remote-group participation, several beta-D-mannoside and beta-D-taloside derivatives were very conveniently obtained in good yields.

  • 12.
    Hamza, Karim
    et al.
    Stockholm Univ, Dept Math & Sci Educ, S-10691 Stockholm, Sweden..
    Piqueras, Jesus
    Stockholm Univ, Dept Math & Sci Educ, S-10691 Stockholm, Sweden..
    Wickman, Per-Olof
    Stockholm Univ, Dept Math & Sci Educ, S-10691 Stockholm, Sweden..
    Angelin, Marcus
    KTH, School of Industrial Engineering and Management (ITM).
    Who Owns the Content and Who Runs the Risk?: Dynamics of Teacher Change in Teacher-Researcher Collaboration2018In: Research in science education, ISSN 0157-244X, E-ISSN 1573-1898, Vol. 48, no 5, p. 963-987Article in journal (Refereed)
    Abstract [en]

    We present analyses of teacher professional growth during collaboration between science teachers and science education researchers, with special focus on how the differential assumption of responsibility between teachers and researchers affected the growth processes. The collaboration centered on a new conceptual framework introduced by the researchers, which aimed at empowering teachers to plan teaching in accordance with perceived purposes. Seven joint planning meetings between teachers and researchers were analyzed, both quantitatively concerning the extent to which the introduced framework became part of the discussions and qualitatively through the interconnected model of teacher professional growth. The collaboration went through three distinct phases characterized by how and the extent to which the teachers made use of the new framework. The change sequences identified in relation to each phase show that teacher recognition of salient outcomes from the framework was important for professional growth to occur. Moreover, our data suggest that this recognition may have been facilitated because the researchers, in initial phases of the collaboration, took increased responsibility for the implementation of the new framework. We conclude that although this differential assumption of responsibility may result in unequal distribution of power between teachers and researchers, it may at the same time mean more equal distribution of concrete work required as well as the inevitable risks associated with pedagogical innovation and introduction of research-based knowledge into science teachers' practice.

  • 13.
    Larsson, Rikard
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Angelin, Marcus
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dynamic Combinatorial Resolution2007In: Materials, Membranes and Processes / [ed] G. Nechifor and M.Barboiu, Bucharest: Printech , 2007, p. 30-65Chapter in book (Other academic)
  • 14.
    Sakulsombat, Morakot
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Angelin, Marcus
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Caraballo, Rémi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    A Dynamic Multicomponent Approach for One-Pot Synthesis of 3-Thioisoindolinones2013In: Israel Journal of Chemistry, ISSN 0021-2148, Vol. 53, no 1-2, p. 127-132Article in journal (Refereed)
    Abstract [en]

    A dynamic multicomponent reaction concept has been successfully applied to the syntheses of 3-thioisoindolinones and tricyclic gamma-lactams. The reactions were efficiently designed and operated in the absence of any catalyst under mild reaction conditions, resulting in the convenient variation of substituents on the N- and S-positions of the target products.

  • 15.
    Sakulsombat, Morakot
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Angelin, Marcus
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Tandem reversible addition-intramolecular lactonization for the synthesis of 3-functionalized phthalides2010In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 51, no 1, p. 75-78Article in journal (Refereed)
    Abstract [en]

    A new tandem process based on reversible nucleophilic addition and intramolecular lactonization of methyl 2-formylbenzoate leads to the efficient synthesis of 3-functionalized phthalides, which are important precursors for the synthesis of quinone skeletons via Hauser–Kraus annulation. The reactions are successfully carried out under mild conditions in single operations.

  • 16.
    Vongvilai, Pornrapee
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Angelin, Marcus
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Larsson, Rikard
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dynamic Combinatorial Resolution: Direct Asymmetric Lipase-Mediated Screening of a Dynamic Nitroaldol Library2007In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, no 6, p. 948-950Article in journal (Refereed)
    Abstract [en]

    (Chemical Equation Presented) A disturbance in the library: The nitroaldol (Henry) reaction was developed as an efficient C-C bond-forming route to dynamic combinatorial libraries (DCLs). These DCLs generated under thermodynamic control were coupled in a one-pot process with kinetically controlled lipase-mediated transesterification (see scheme). The asymmetric resolution of the DCLs by the enzyme led to enantiomerically pure β-nitroacetates in high yield.

  • 17.
    Zhang, Yan
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Angelin, Marcus
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Larsson, Rikard
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Albers, Antonia
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Simons, Adrian
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Tandem driven dynamic self-inhibition of acetylcholinesterase2010In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 46, no 44, p. 8457-8459Article in journal (Refereed)
    Abstract [en]

    A concept of tandem driven dynamic self-inhibition is demonstrated through dynamic inhibitors of acetylcholinesterase (AChE) using reversible transthiolesterification.

1 - 17 of 17
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