Direct, stereospecific generation of (Z)-disubstituted allylic alcohols

被引：37

作者：

Jeon, Sang-Jin ^{[1
]}

Fisher, Ethan L. ^{[1
]}

Carroll, Patrick J. ^{[1
]}

Walsh, Patrick J. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, P Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 30期

关键词：

D O I：

10.1021/ja061973n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 α- or β-oxygenated aldehydes proceeds with diastereoselectivities between 6:1 and 18:1. The anti-Felkin product is obtained in most cases. Copyright © 2006 American Chemical Society.

引用

页码：9618 / 9619

页数：2

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