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Migratory Dynamic Kinetic Resolution of Carbocyclic Allylic Alcohols

Chicco Manzuna Sapu, Tamás Görbe, Richard Lihammar, Jan-E. Bäckvall* and Jan Deska*

*Department of Organic Chemistry, Stockholms Universitet, 10691 Stockholm, Sweden, Department für Chemie, Universität zu Köln, 50939 Cologne, Germany, Email: jeborgan.su.se, jan.deskauni-koeln.de

C. M. Sapu, T. Görbe, R. Lihammar, J.-E. Bäckvall, J. Deska, Org. Lett., 2014, 16, 5952-5955.

DOI: 10.1021/ol502979g (free Supporting Information)


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Abstract

An enzyme acylation catalyst and a heterogeneous Brønsted acid as an isomerization/racemization catalyst enables a migratory dynamic kinetic resolution of readily available carbocyclic tertiary carbinols to yield allylic esters in high yield with excellent stereoselectivity. An easy-to-use teabag setup combining resin-bound catalysts, a biphasic isooctane-water solvent system, and a highly lipophilic acyl donor efficiently suppresses side reactions.

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Key Words

allylic alcohols


ID: J54-Y2014