Tandem reactions with chiral enolates: preparation of allylic alcohols via trapping with vinyl oxiranes

Welker, Matthias; Woodward, Simon; Alexakis, Alexandre

doi:10.1021/ol9027682

Scientific article

English

Tandem reactions with chiral enolates: preparation of allylic alcohols via trapping with vinyl oxiranes

ContributorsWelker, Matthias; Woodward, Simon; Alexakis, Alexandre

Published inOrganic letters, vol. 12, no. 3, p. 576-579

Publication date2010

Abstract

An opening of vinyl oxiranes has been accomplished with Zn and Al enolates resulting from asymmetric conjugate addition reactions on cyclic enones. This novel tandem procedure affords the adducts in moderate to good yields, enantioselectivities up to 98%, and moderate to good cis/trans selectivities. This provides potentially useful synthetic substrates to prepare complex bicyclic compounds.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

WELKER, Matthias, WOODWARD, Simon, ALEXAKIS, Alexandre. Tandem reactions with chiral enolates: preparation of allylic alcohols via trapping with vinyl oxiranes. In: Organic letters, 2010, vol. 12, n° 3, p. 576–579. doi: 10.1021/ol9027682

Article (Published version)

Identifiers

PID : unige:5224
DOI : 10.1021/ol9027682

Journal ISSN1523-7052

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Tandem reactions with chiral enolates: preparation of allylic alcohols via trapping with vinyl oxiranes

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