Copper(I) tert-butoxide-promoted 1,4 C-sp2-to-O silyl migration: Stereospecific allylation of (Z)-gamma-trimethylsilyl allylic alcohols

Citation
H. Taguchi et al., Copper(I) tert-butoxide-promoted 1,4 C-sp2-to-O silyl migration: Stereospecific allylation of (Z)-gamma-trimethylsilyl allylic alcohols, ORG LETT, 3(23), 2001, pp. 3811-3814
Citations number
43
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
1523-7060 → ACNP
Volume
3
Issue
23
Year of publication
2001
Pages
3811 - 3814
Database
ISI
SICI code
1523-7060(20011115)3:23<3811:CT1CSM>2.0.ZU;2-A
Abstract
[GRAPHICS] The cyclic silyl ethers, 2,2-dimethyl-1-oxa-2-slia-3-cyclopentenes, were pr oduced by the treatment of (2)-gamma -trimethylsilyl allylic alcohols with a catalytic or stoichiometric amount of lithium tort-butoxide. On the other hand, successive treatment of the alcohols with copper(l) tert-butoxide an d allylic halides followed by the tetrabutylammmonium fluoride assisted hyd rolysis produced the allylation products, 2,5-alkadien-1-ols, with complete retention of configuration of the double bond.