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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, Email: pwalshsas.upenn.edu

S.-J. Jeon, E. L. Fischer, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2006, 128, 9618-9619.

DOI: 10.1021/ja061973n (free Supporting Information)


Abstract

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.

see article for more reactions



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

Y. K. Chen, P. J. Walsh, J. Am. Chem. Soc., 2004, 126, 3702-3703.


Key Words

Allylic Alcohols, Dienes


ID: J48-Y2006-2310