Efficient Preparation of Optically Pure C2-Symmetrical Cyclic Amines for Chiral Auxiliary

Mitsuo Sato; Yasuhiko Gunji; Taketo Ikeno; Tohru Yamada

doi:10.1055/s-2004-822366

PAPER

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;

Abstract

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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

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References

<A NAME="RC01204SS-1">1</A> Whitesell JK. Chem. Rev. 1989, 89: 1581

<A NAME="RC01204SS-2">2</A> Whitesell JK. Felman SW. J. Org. Chem. 1977, 42: 1663

<A NAME="RC01204SS-3A">3a</A> Porter NA. Lacher B. Chang VH.-T. Magnin DR. J. Am. Chem. Soc. 1989, 111: 8309

<A NAME="RC01204SS-3B">3b</A> Porter NA. Scott DM. Lacher B. Giese B. Zeitz HG. Lindner HJ. J. Am. Chem. Soc. 1989, 111: 8311

<A NAME="RC01204SS-3C">3c</A> Stafford JA. Heathcock CH. J. Org. Chem. 1990, 55: 5433

<A NAME="RC01204SS-3D">3d</A> Defoin A. Brouillard-Poichet A. Streith J. Helv. Chim. Acta 1991, 74: 103

<A NAME="RC01204SS-3E">3e</A> Yamazaki T. Welch JT. Plummer JS. Gimi R. Tetrahedron Lett. 1991, 32: 4267

<A NAME="RC01204SS-3F">3f</A> Honda T. Kimura N. Tsubuki M. Tetrahedron: Asymmetry 1993, 4: 21

<A NAME="RC01204SS-4A">4a</A> Chong JM. Clarke IS. Koch I. Olbach PC. Taylor NJ. Tetrahedron: Asymmetry 1995, 6: 409

<A NAME="RC01204SS-4B">4b</A> Aldous DJ. Dutton WM. Steel PG. Tetrahedron: Asymmetry 2000, 11: 2455

<A NAME="RC01204SS-5A">5a</A> Poerwono H. Higashiyama K. Yamauchi T. Takahashi H. Heterocycles 1997, 46: 385

<A NAME="RC01204SS-5B">5b</A> Pache S. Botuha C. Franz R. Kündig EP. Helv. Chim. Acta 2000, 83: 2436

<A NAME="RC01204SS-6">6</A> Synthesis of trans-2,4-diaryl azetidine was reported: Powell BF. Reichenthal J. Overberger CG. Anselme JP. J. Heterocycl. Chem. 1980, 17: 219

<A NAME="RC01204SS-7A">7a</A> Ohtsuka Y. Kubota T. Ikeno T. Nagata T. Yamada T. Synlett 2000, 535

<A NAME="RC01204SS-7B">7b</A> Yamada T. Nagata T. Sugi KD. Yorozu K. Ikeno T. Ohtsuka Y. Miyazaki D. Mukaiyama T. Chem.-Eur. J. 2003, 9: 4485

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]

<A NAME="RC01204SS-9">9</A> Nevar NM. Kel’in AV. Kulinkovich OG. Synthesis 2000, 1259

<A NAME="RC01204SS-10">10</A> Conant JB. Lutz RE. J. Am. Chem. Soc. 1923, 45: 1303

<A NAME="RC01204SS-11">11</A> Bailey PS. Lutz RE. J. Am. Chem. Soc. 1948, 70: 2412

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

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