First anionic silyl migration from sp2 carbon to carbonyl oxygen. Stereospecific allylation of (Z)-beta-trimethylsilyl-alpha,beta-unsaturated ketones.
1,4-Silyl migration from sp2 carbon to carbonyl oxygen proceeded by the treatment of (Z)-beta-trimethylsilyl-alpha,beta-unsaturated ketones with copper(I) tert-alkoxide to afford vinylmetal species, which reacted with allylic halides to produce enol trimethylsilyl ethers of beta-alk-2-enyl-alpha,beta-unsaturated ketones with complete retention of configuration.
Taguchi
Haruhiko
H
Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan.
Miyashita
Hiroko
H
Tsubouchi
Akira
A
Takeda
Takeshi
T