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Chem Commun (Camb). 2002 Oct 7;(19):2218-9.

First anionic silyl migration from sp2 carbon to carbonyl oxygen. Stereospecific allylation of (Z)-beta-trimethylsilyl-alpha,beta-unsaturated ketones.

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1
Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan.

Abstract

1,4-Silyl migration from sp2 carbon to carbonyl oxygen proceeded by the treatment of (Z)-beta-trimethylsilyl-alpha,beta-unsaturated ketones with copper(I) tert-alkoxide to afford vinylmetal species, which reacted with allylic halides to produce enol trimethylsilyl ethers of beta-alk-2-enyl-alpha,beta-unsaturated ketones with complete retention of configuration.

PMID:
12397986
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