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Synthesis 2004(9): 1504-1508
DOI: 10.1055/s-2004-822404
DOI: 10.1055/s-2004-822404
PAPER
© Georg Thieme Verlag Stuttgart · New York
Copper(I) tert-Butoxide-Promoted Allylation of β-Triphenylsilyl Allylic Alcohols via 1,3 C sp² -to-O Silyl Migration
Further Information
Received
2 May 2004
Publication Date:
08 June 2004 (online)
Publication History
Publication Date:
08 June 2004 (online)
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 Csp2-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
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