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Organocatalytic Asymmetric Synthesis of Trifluoromethyl-substituted Diarylpyrrolines: Enantioselective Conjugate Cyanation of β-Aryl-β-trifluoromethyl-disubstituted Enones

Authors

  • Hiroyuki Kawai,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
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  • Satoshi Okusu,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
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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)
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  • Hiroyasu Sato,

    1. Rigaku Corporation, 3-9-12 Mastubara-cho, Akishima, Tokyo 196-8666 (Japan)
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  • Dr. Motoo Shiro,

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

    Corresponding author
    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
    • Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
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  • Support was provided by the Grants-in-Aid for Scientific Research (21390030, 23915014, 22106515, Project No. 2105: Organic Synthesis Based on Reaction Integration). We also thank the Asahi Glass Foundation for support in part.

Abstract

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Feinjustierte Katalyse: Die durch eine China-Alkaloid katalysierte Titelreaktion gelang in hohen Ausbeuten und Enantioselektivitäten und liefert Schlüsselintermediate für das biologisch wichtige Pyrrolin 2, das ein trifluormethyliertes quartäres Stereozentrum enthält. Ether-Katalysatoren (1) sind in dieser Umwandlung effizienter als die konventionellen Hydroxyspezies.

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