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Catalytic Enantioselective Trifluoromethylation of Azomethine Imines with Trimethyl(trifluoromethyl)silane

Authors

  • 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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  • 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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  • 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 by a Grant-in-Aid for Scientific Research on Priority Areas “Advanced Molecular Transformations of Carbon Resources” from the Ministry of Education, Culture, Sports, Science, and Technology Japan. We also thank TOSOH F-TECH INC. for a gift of Me3SiCF3.

Abstract

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It′s a cinch! The title reaction with azomethine imines 1 uses an operationally simple procedure, based on the combination of the bromide salt of cinchona alkaloids (3) and KOH. The procedure is reliable and general. Trifluoromethyl-substituted amines can be accessed by a two-step deprotection of the product (S)-2.

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