Direct, Stereospecific Generation of (Z)-Disubstituted Allylic Alcohols

Sang-Jin Jeon, Ethan L. Fisher, Patrick J. Carroll, and Patrick J. Walsh*
P. Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323
J. Am. Chem. Soc., 2006, 128 (30), pp 9618–9619
DOI: 10.1021/ja061973n
Publication Date (Web): July 12, 2006
Copyright © 2006 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

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.

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History

  • Published In Issue August 02, 2006
  • Received March 31, 2006

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