PAPER	Synthesis 2004: 1504-1508   DOI: 10.1055/s-2004-822404
© Georg Thieme Verlag Stuttgart · New York
Copper(I) tert-Butoxide-Promoted Allylation of β-Triphenylsilyl Allylic Alcohols­ via 1,3 Csp²-to-O Silyl Migration
Akira Tsubouchi, Miki Itoh, Kotaro Onishi, Takeshi Takeda*
Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan Fax: +81(42)3887034; e-Mail: takeda-t@cc.tuat.ac.jp;
Received 2 May 2004

Abstract

The substitution of the silyl group in vinylsilanes by an allylic group proceeded when β-triphenylsilylallyl alcohols were treated with copper(I) tert-butoxide and allylic halides. This reaction is the first synthetic application of 1,3 C^sp2-to-O silyl migration which provides a useful method for generation of vinyl anion equivalents.

Key words

allylations - allylic alcohols - copper alkoxides - silyl rearrangemen­t - silyl ethers