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Scientific article
Letter
English

Tandem asymmetric conjugate addition-silylation of enantiomerically enriched zinc enolates. Synthetic importance and mechanistic implications

Contributors

Knopff, Oliver; Alexakis, Alexandre

Published in

Organic letters, vol. 4, no. 22, p. 3835-3837

Publication date

2002

Abstract

The zinc enolates, resulting from the copper-catalyzed enantioselective conjugate addition of dialkyl zinc reagents to cyclic and acyclic enones, could be trapped, quantitatively, as silyl enol ethers with TMSOTf in apolar solvents or with TMSCl and NEt3. These enantiomerically enriched silyl enol ethers were submitted to four synthetic transformations to show their synthetic utility. The zinc enolates obtained from acyclic enones were found to be configurationally stable, as shown by the stereochemistry of the silyl enol ethers.

UNIGE affiliation entities

Citation (ISO format)

KNOPFF, Oliver, ALEXAKIS, Alexandre. Tandem asymmetric conjugate addition-silylation of enantiomerically enriched zinc enolates. Synthetic importance and mechanistic implications. In: Organic letters, 2002, vol. 4, n° 22, p. 3835–3837. doi: 10.1021/ol026644o

Main files (1)

Article (Published version)

Identifiers

Journal ISSN

1523-7052
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Technical informations

Creation

21/06/2010 14:15:46

First validation

21/06/2010 14:15:46

Update

14/03/2023 15:47:48

Status update

14/03/2023 15:47:48

Last indexation

10/06/2025 21:35:48
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