Copper(I) tert-Butoxide-Promoted Allylation of β-Triphenylsilyl Allylic Alcohols via 1,3 C^sp2-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, Email: takeda-tcc.tuat.ac.jp

A. Tsubouchi, M. Itoh, K. Onishi, T. Takeda, Synthesis, 2004, 1504-1508.

DOI: 10.1055/s-2004-822404

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Abstract

Use of copper(I) tert-butoxide and allylic halides enables the substitution of the silyl group in vinylsilanes by an allylic group. This synthetic application of a 1,3 C^sp2-to-O silyl migration provides a useful method for the generation of vinyl anion equivalents.

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proposed mechanism

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Key Words

allylations, allylic alcohols, copper alkoxides, silyl rearrangement, silyl ethers, Brook rearrangement

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ID: J66-Y2004-2440