en
Scientific article
Letter
English

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

Published inOrganic letters, vol. 4, no. 22, p. 3835-3837
Publication date2002
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.

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
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ISSN of the journal1523-7052
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