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Synthesis 2004(9): 1434-1438  
DOI: 10.1055/s-2004-822366
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Preparation of Optically Pure C 2 -Symmetrical Cyclic Amines for Chiral Auxiliary

Mitsuo Sato, Yasuhiko Gunji, Taketo Ikeno, Tohru Yamada*
Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
Fax: +81(45)5661716; e-Mail: yamada@chem.keio.ac.jp;
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Publication History

Received 2 January 2004
Publication Date:
10 May 2004 (online)

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Abstract

Optically pure C 2 -symmetrical amines were efficiently synthesized from the corresponding diols obtained from the enantioselective borohydride reduction of the diketones catalyzed by the optically active b-ketoiminato cobalt(II) complex.

Key words

asymmetric reduction - chiral diols - cyclic chiral amines - borohydride - cobalt

8

It was reported that the chiral oxazaborolidine did not work for the reduction of 1,4-bis(2-naphthyl)-1,4-butanedione. See ref. [4b]