Synfacts 2008(4): 0379-0379  
DOI: 10.1055/s-2008-1042785
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of trans-2,6-Disubstituted Piperazines

Contributor(s): Mark Lautens, Frédéric Ménard
B. M. Cochran, F. E. Michael*
University of Washington, Seattle, USA
Further Information

Publication History

Publication Date:
19 March 2008 (online)


A short and operationally simple synthesis of enantiopure trans-2,6-substituted piperazines is reported with excellent yields and high diastereoselectivity. Cyclization precursors 1 are readily available from chiral amino alcohols and simple allylamines by an improved practical protocol. The strategy takes advantage of the ­numerous established methods to prepare chiral amino alcohols.