doi: 10.1021/ja061973n.
Direct, stereospecific generation of (Z)-disubstituted allylic alcohols
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- PMID: 16866501
- DOI: 10.1021/ja061973n
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Direct, stereospecific generation of (Z)-disubstituted allylic alcohols
J Am Chem Soc.
.
Abstract
A one-pot method to prepare highly functionalized (Z)-disubstituted allylic alcohols is introduced. Hydroboration of a variety of 1-bromo-1-acetylenes with dicyclohexyl borane, reaction with t-BuLi, and transmetalation to zinc generates a (Z)-disubstituted vinylzinc reagent. In situ reaction of this reagent with aldehydes generates (Z)-disubstituted allylic alcohols in high yields (81-97%). Addition to chiral protected alpha- or beta-oxygenated aldehydes proceeds with diastereoselectivities between 6:1 and 18:1. The anti-Felkin product is obtained in most cases.
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