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Letter

Design and Synthesis of Novel C₂-Symmetric Chiral Piperazines and an Application to Asymmetric Acylation of σ-Symmetric 1,2-Diols

Supporting Info

Daisuke Nakamura,^‡ Kiyomi Kakiuchi,^‡ Kenji Koga,^‡ and Ryuichi Shirai*^‡^†

Research and Education Center for Materials Science and Graduate School of Materials Science, Nara Institute of Science and Technology, Takayama, Ikoma-shi, Nara 630-0192, Japan, and Faculty of Pharmaceutical Sciences, Doshisha Women's College of Liberal Arts, Kodo, Kyotanabe-shi, Kyoto 610-0395, Japan

Org. Lett., 2006, 8 (26), pp 6139–6142

DOI: 10.1021/ol0626387

Publication Date (Web): November 24, 2006

‡

Nara Institute of Science and Technology.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

†

Present address: Doshisha Women's College of Liberal Arts.

, rshirai@dwc.doshisha.ac.jp

Abstract

A novel alicyclic chiral C₂-symmetric piperazine, (S,S)-7, is designed and synthesized from l-proline. Benzoylation of a series of cyclic and acyclic meso-1,2-diols with a catalytic amount of (S,S)-7 and CuCl₂ provided optically active monobenzoates with high enantioselectivity.

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Published In Issue December 21, 2006
Received October 27, 2006

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Letter

Design and Synthesis of Novel C₂-Symmetric Chiral Piperazines and an Application to Asymmetric Acylation of σ-Symmetric 1,2-Diols