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Cofactor-Controlled Chirality of Tropoisomeric Ligand
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0002-7552-1076
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2016 (English)In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 35, no 11, 1956-1963 p.Article in journal (Refereed) Published
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Text
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.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2016. Vol. 35, no 11, 1956-1963 p.
Keyword [en]
Carboxylation, Conformations, Ions, Negative ions, Palladium compounds, Substitution reactions, Allylic substitution, Anion receptor, Benzylamines, Chiral conformations, Olefin complexes, Palladium allyl complexes, Phosphate anions, Phosphite ligands
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-189668DOI: 10.1021/acs.organomet.6b00265ISI: 000377925600042Scopus ID: 2-s2.0-84974712815OAI: oai:DiVA.org:kth-189668DiVA: diva2:949060
Funder
Wenner-Gren Foundations
Note

QC 20160714

Available from: 2016-07-15 Created: 2016-07-11 Last updated: 2016-07-15Bibliographically approved

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