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

Contributors

Welker, Matthias; Woodward, Simon; Alexakis, Alexandre

Published in

Organic letters, vol. 12, no. 3, p. 576-579

Publication date

2010

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.

UNIGE 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 ISSN

1523-7052

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Creation

17/02/2010 10:37:00

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17/02/2010 10:37:00

Update

14/03/2023 15:24:11

Status update

14/03/2023 15:24:11

Last indexation

29/10/2024 13:00:58

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

Contributors

Published in

Publication date

Abstract

UNIGE affiliation entities

Citation (ISO format)

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Identifiers

Journal ISSN

Technical informations

Creation

First validation

Update

Status update

Last indexation