Synfacts 2006(10): 1056-1056  
DOI: 10.1055/s-2006-949303
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Direct Preparation of (Z)-Disubstituted Allylic Alcohols

Contributor(s): Paul Knochel, Andrei Gavryushin
S.-J. Jeon, E. L. Fisher, P. J. Carroll, P. J. Walsh*
University of Pennsylvania, Philadelphia, USA
Further Information

Publication History

Publication Date:
21 September 2006 (online)

Significance

The authors describe a simple one-pot protocol for the preparation of (Z)-disubstituted allylic alcohols from 1-bromoalkynes and aldehydes. Complete stereoselectivity and good functional-group compatibility are observed. In the case of chiral aldehydes, satisfactory diastereoselectivities were obtained in many cases. This synthetic protocol is simple and uses readily available starting materials. This reaction may become a useful tool for the stereoselective synthesis of complex organic molecules.