A one-pot multicomponent coupling reaction for the stereocontrolled synthesis of (Z)-trisubstituted allylic alcohols

被引:49
作者
Chen, YK [1 ]
Walsh, PJ [1 ]
机构
[1] Univ Penn, P Roy & Diana T Vagelos Labs, Dept Chem, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ja0396145
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this Communication, we outline a new one-pot, multicomponent coupling reaction that allows easy access to (Z)-trisubstituted allylic alcohols. Our strategy is based on E to Z isomerization of the 1-bromo-1-dialkylvinylborane upon reaction with dialkylzinc reagents, and subsequent transmetalation to give (Z)-trisubstituted vinylzinc species. In situ trapping of the reactive vinylzinc intermediates with aldehydes furnished a series of (Z)-trisubstituted allylic alcohols. This method represents a viable alternative to the Still?Gennari modification of the HWE olefination reaction, and it has the advantage that it allows coupling of larger fragments. Copyright © 2004 American Chemical Society.
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页码:3702 / 3703
页数:2
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