Copper(I)tert-Butoxide-Promoted 1,4 Csp2-to-O Silyl Migration: Generation of Vinyl Copper Equivalents and Their Stereospecific Cross-Coupling with Allylic, Aryl, and Vinylic Halides
- 1 November 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (24) , 8450-8456
- https://doi.org/10.1021/jo025973r
Abstract
Successive treatment of the (Z)-γ-trimethylsilyl allylic alcohols with copper(I) tert-butoxide and allylic halides followed by the tetrabutylammonium fluoride-assisted hydrolysis produced the allylation products, 2,5-alkadien-1-ols, with complete retention of configuration. Similar treatment of the organometallic intermediates with aryl and vinylic halides in the presence of palladium(0) catalyst gave the corresponding cross-coupling products in good yields. The stereoselective preparation of the starting materials is also described.Keywords
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