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Synfacts 2007(11): 1136-1136  
DOI: 10.1055/s-2007-991294
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Chiral Piperazines

Contributor(s): Victor Snieckus, Jignesh J. Patel
J. S. Nakhla, J. P. Wolfe*
University of Michigan, Ann Arbor, USA
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Publication History

Publication Date:
23 October 2007 (online)

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Significance

Described here is a concise and modular asymmetric synthesis of N-aryl-2,6-di­substituted piperazine via a Pd-catalyzed carbo­amination reaction. The process allows the stereo­selective preparation of piperazine derivatives with different N1, C2, N4 and C6 groups starting from commercial amino acids. A 4:1 ratio of Pd2(dba)3 and P(2-furyl)3 was found to be the best catalyst system in order to suppress the formation of the major side products B and C. Aryl bromides containing EWG and EDG were found to be effective coupling partners.