Copper(I) tert-butoxide-promoted 1,4 C(sp(2))-to-O silyl migration: stereospecific allylation of (Z)-gamma-trimethylsilyl allylic alcohols.
[reaction--see text] The cyclic silyl ethers, 2,2-dimethyl-1-oxa-2-sila-3-cyclopentenes, were produced by the treatment of (Z)-gamma-trimethylsilyl allylic alcohols with a catalytic or stoichiometric amount of lithium tert-butoxide. On the other hand, successive treatment of the alcohols with copper(I) tert-butoxide and allylic halides followed by the tetrabutylammmonium fluoride assisted hydrolysis produced the allylation products, 2,5-alkadien-1-ols, with complete retention of configuration of the double bond.
Taguchi
H
H
Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan.
Ghoroku
K
K
Tadaki
M
M
Tsubouchi
A
A
Takeda
T
T