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Migratory Dynamic Kinetic Resolution of Carbocyclic Allylic Alcohols
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2014 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, no 22, 5952-5955 p.Article in journal (Refereed) Published
Abstract [en]

A novel migratory dynamic kinetic resolution based on the interplay between an enzyme acylation catalyst and a heterogeneous Bronsted acid as an isomerization/racemization catalyst gives rise to carbocyclic allylic esters with excellent stereoselectivity from readily available tertiary carbinols. An easy-to-use teabag setup combining resin-bound catalysts, a biphasic isooctanewater solvent system, and a highly lipophilic acyl donor efficiently suppresses side reactions and allows for the preparation of functionalized carbocyclic building blocks in high yields and optical purity.

Place, publisher, year, edition, pages
2014. Vol. 16, no 22, 5952-5955 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-121784DOI: 10.1021/ol502979gISI: 000345470000033OAI: oai:DiVA.org:su-121784DiVA: diva2:861407
Funder
German Research Foundation (DFG), DE1599/4-1Swedish Research CouncilKnut and Alice Wallenberg Foundation
Available from: 2015-10-16 Created: 2015-10-16 Last updated: 2017-12-01Bibliographically approved

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Görbe, TamásLihammar, RichardBäckvall, Jan-Erling
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