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Origins of Stereoselectivity in Peptide-Catalyzed Kinetic Resolution of Alcohols
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 52016 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 6, no 2, p. 1165-1171Article in journal (Refereed) Published
Abstract [en]

The origin of the stereoselectivity of the tetrapeptide-catalyzed kinetic resolution of trans-2-N-acetamidocyclohexanol is investigated by means of density functional theory calculations. Transition states for the functionalization of both (R,R) and (S,S) substrates were optimized considering all possible conformers. Due to the flexibility of the peptidic catalyst, a large number of transition states had to be located, and analysis of the geometries and energies allowed for the identification of the main factors that control the stereo selectivity.

Place, publisher, year, edition, pages
2016. Vol. 6, no 2, p. 1165-1171
Keywords [en]
organocatalysis, enantioselectivity, acylation, density functional theory, transition state, reaction mechanism
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-127865DOI: 10.1021/acscatal.5b02131ISI: 000369774900078OAI: oai:DiVA.org:su-127865DiVA, id: diva2:940550
Available from: 2016-06-21 Created: 2016-03-14 Last updated: 2017-11-28Bibliographically approved

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