A One-Pot Multicomponent Coupling Reaction for the Stereocontrolled Synthesis of (Z)-Trisubstituted Allylic Alcohols

Young K. Chen and Patrick J. Walsh*
P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323
J. Am. Chem. Soc., 2004, 126 (12), pp 3702–3703
DOI: 10.1021/ja0396145
Publication Date (Web): March 5, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, pwalsh@sas.upenn.edu

Abstract

Abstract Image

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.

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History

  • Published In Issue March 31, 2004
  • Received November 15, 2003

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