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Germanium(II)-Mediated Reductive Mannich-Type Reaction of α-Bromoketones to N-Alkylimines

Authors

  • Shin-ya Tanaka,

    1. Department of Applied Chemistry, Center for Atomic and Molecular Technologies (CAMT), Graduate School of Engineering, Osaka University, 2-1, Yamada-oka, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7387
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  • Nobuo Tagashira,

    1. Department of Applied Chemistry, Center for Atomic and Molecular Technologies (CAMT), Graduate School of Engineering, Osaka University, 2-1, Yamada-oka, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7387
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  • Kouji Chiba,

    1. Department of Applied Chemistry, Center for Atomic and Molecular Technologies (CAMT), Graduate School of Engineering, Osaka University, 2-1, Yamada-oka, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7387
    2. Science and Technology System Division, Ryoka Systems Inc., 1-28-38 Shinkawa, Chuo-ku, Tokyo 104-0033 (Japan)
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  • Makoto Yasuda Dr.,

    1. Department of Applied Chemistry, Center for Atomic and Molecular Technologies (CAMT), Graduate School of Engineering, Osaka University, 2-1, Yamada-oka, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7387
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  • Akio Baba Prof. Dr.

    1. Department of Applied Chemistry, Center for Atomic and Molecular Technologies (CAMT), Graduate School of Engineering, Osaka University, 2-1, Yamada-oka, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7387
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  • This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of the Japanese Government. S.T. expresses his special thanks for Research Fellowships of the Japan Society for JSPS Research Fellowships for Young Scientists.

Abstract

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Das vielseitige Metall Germanium vermittelt eine neuartige Mannich-Reaktion von α-Bromketonen mit einfachen N-Alkyliminen (siehe Schema). Germanium(II) wirkt bei der Bildung eines Nucleophils für die C-C-Verknüpfung als Reduktionsmittel, und das Mannich-Addukt wird durch ein Germaniumzentrum stabilisiert. Verschiedene N-Alkylaldimine, darunter enolisierbare Imine und Formaldimine, gehen die Reaktion ein.

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