Journal of the American Chemical Society 2004-03-31

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

Young K Chen, Patrick J Walsh

Index: J. Am. Chem. Soc. 126(12) , 3702-3, (2004)

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Abstract

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.