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Note | Regular issue | Vol 75, No. 6, 2008, pp.1493-1501
Published online, 22nd February, 2008
DOI: 10.3987/COM-08-11328
Stereoselective Synthesis of a Novel Chiral Piperazine

Satoshi Kojima,* Takashi Chabayashi, Yasuhiro Umeda, Akihisa Iwamoto, Kazuhisa Tanabe, and Katsuo Ohkata

*Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan

Abstract

(2S,6S)-2,4,6-Tris(phenylmethyl)piperazine was prepared in 11 steps and 53% overall yield from S-phenylalanine. Key steps in the synthesis involved reductive amination to introduce an ethoxycarbonylmethyl group on to the secondary nitrogen of the product and selective alkylation to introduce a benzyl group with complete diastereoselectivity.