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

Haruhiko Taguchi; Hiroko Miyashita; Akira Tsubouchi; Takeshi Takeda

doi:10.1039/B207325K

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

Haruhiko Taguchi,^a Hiroko Miyashita,^a Akira Tsubouchi^a and Takeshi Takeda*^a

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* Corresponding authors

^a Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan
E-mail: takeda-t@cc.tuat.ac.jp
Fax: +81 42 388 7034
Tel: +81 42 388 7034

Abstract

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

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Article information

DOI: https://doi.org/10.1039/B207325K
Article type: Communication
Submitted: 25 Jul 2002
Accepted: 20 Aug 2002
First published: 05 Sep 2002

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Chem. Commun., 2002, 2218-2219

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

H. Taguchi, H. Miyashita, A. Tsubouchi and T. Takeda, Chem. Commun., 2002, 2218 DOI: 10.1039/B207325K

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Chemical Communications

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

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

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