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Catalytic Enantioselective Michael Addition of 1-Fluorobis(phenylsulfonyl)methane to α,β-Unsaturated Ketones Catalyzed by Cinchona Alkaloids

Authors

  • 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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  • 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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  • Satoshi Mizuta 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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  • 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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  • Takeshi Toru 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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  • Motoo Shiro Dr.

    1. Rigaku Corporation, 3-9-12 Matsubara-cho, Akishima, Tokyo 196-8666 (Japan)
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  • Support was provided by a Grant-in-Aid for Scientific Research (B) (19390029) for Scientific Research on Priority Areas “Advanced Molecular Transformations of Carbon Resources” from the Ministry of Education, Culture, Sports, Science, and Technology Japan (19020024).

Abstract

original image

Ammoniumsalze von China-Alkaloiden mit sperrigen Substituenten katalysieren die hoch enantioselektive konjugierte Addition von 1-Fluorbis(phenylsulfonyl)methan an α,β-ungesättigte Ketone, die in hohen Ausbeuten zu den Michael-Addukten führt (siehe Schema). Ausgehend von diesen Addukten können chirale Monofluormethylverbindungen synthetisiert werden.

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