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Enantioselective Synthesis of Trifluoromethyl-Substituted 2-Isoxazolines: Asymmetric Hydroxylamine/Enone Cascade Reaction

Authors

  • Kazutaka Matoba,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442
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  • Hiroyuki Kawai,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442
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  • Tatsuya Furukawa,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442
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  • Akihiro Kusuda,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442
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  • Etsuko Tokunaga,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442
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  • Shuichi Nakamura Dr.,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442
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  • Motoo Shiro Dr.,

    1. Rigaku Corporation, 3-9-12 Mastubara-cho, Akishima Tokyo 196-8666 (Japan)
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  • Norio Shibata Prof.

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442
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  • Support was provided by KAKENHI (21390030, 22106515). The corresponding author thanks the JSPS for financial support of this work in part through a Joint Research Project between Japan and France.

Abstract

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Cuts both ways: The title reaction consists of an addition/cyclization/dehydration sequence and affords the biologically important chiral 3,5-diaryl-5-(trifluoromethyl)-2-isoxazolines 1 in excellent yields with high ee values. The flexibility of accessing either the S or R enantiomers of the products has been achieved by the appropriate choice of phase-transfer catalyst (2).

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