Copper(I) tert-Butoxide-Promoted 1,4 Csp2-to-O Silyl Migration: Stereospecific Allylation of (Z)-γ-Trimethylsilyl Allylic Alcohols
Haruhiko Taguchi, Kazushi Ghoroku, Makoto Tadaki, Akira Tsubouchi and Takeshi Takeda*
*Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan
H. Taguchi, K. Ghoroku, M. Tadaki, A. Tsubouchi, T. Takeda, Org. Lett., 2001, 3, 3811-3814.
DOI: 10.1021/ol016837w
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Abstract
Treatment of (Z)-γ-trimethylsilyl allylic alcohols with a catalytic or stoichiometric amount of lithium tert-butoxide provides cyclic silyl ethers. A subsequent reaction with allylic halides followed by tetrabutylammmonium fluoride assisted hydrolysis produces 2,5-alkadien-1-ols with complete retention of configuration of the double bond.
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Key Words
ID: J54-Y2001
