Synfacts 2007(4): 0392-0392  
DOI: 10.1055/s-2007-968336
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Epoxidation of Homoallylic Alcohols

Contributor(s): Mark Lautens, Praew Thansandote
W. Zhang, H. Yamamoto*
The University of Chicago, USA
Further Information

Publication History

Publication Date:
23 March 2007 (online)

Significance

The design of a new chiral bishydroxamic acid ligand has resulted in its excellent utility in vanadium-catalyzed asymmetric epoxidation of alcohols. Cumene hydroperoxide is used as the epoxidizing agent and epoxidation can occur with as low as 0.5-1 mol% catalyst loadings at room temperature. Both trans and cis homoallylic alcohols can be epoxidized in excellent yields and enantioselectivities. Extension of this catalyst system to the kinetic resolution of homoallylic alcohols produced highly enantiopure starting alcohols and epoxy alcohols.