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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
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Publikationsdatum:
19. März 2008 (online)

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Significance

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.