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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, Email: pwalshsas.upenn.edu

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

DOI: 10.1021/ja0396145 (free Supporting Information)


Abstract

An easy access to (Z)-trisubstituted allylic alcohols is based on E to Z isomerization of 1-bromo-1-dialkylvinylboranes upon reaction with dialkylzinc reagents. Subsequent transmetalation to give (Z)-trisubstituted vinylzinc species is followed by trapping with aldehydes to furnish a series of (Z)-trisubstituted allylic alcohols.

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proposed mechanism

proposed mechanism



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

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


Key Words

Allylic Alcohols, Alkenes


ID: J48-Y2004-1440