title: Copper(I) tert-butoxide-promoted 1,4 C(sp(2))-to-O silyl migration: stereospecific allylation of (Z)-gamma-trimethylsilyl allylic alcohols.
abstract: [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.
authors.affiliation: Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Taguchi
authors.forename: K
authors.initials: K
authors.lastname: Ghoroku
authors.forename: M
authors.initials: M
authors.lastname: Tadaki
authors.forename: A
authors.initials: A
authors.lastname: Tsubouchi
authors.forename: T
authors.initials: T
authors.lastname: Takeda