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An Achiral-Acid-Induced Switch in the Enantioselectivity of a Chiral cis-Diamine-Based Organocatalyst for Asymmetric Aldol and Mannich Reactions

Authors

  • Dr. Shin A. Moteki,

    1. Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan)
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  • Jianwei Han,

    1. Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan)
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  • Satoru Arimitsu,

    1. Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan)
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  • Dr. Matsujiro Akakura,

    1. Department of Chemistry, Aichi University of Education, Igaya-cho, Kariya 448-8542 (Japan)
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  • Dr. Keiji Nakayama,

    1. Process Technology Research Laboratories, Daiichi Sankyo Co., LTD, Hiratsuka, Kanagawa 254-0014 (Japan)
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  • Prof. Dr. Keiji Maruoka

    Corresponding author
    1. Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan)
    • Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan)
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  • This work was partially supported by a Grant-in-Aid for Scientific Research from MEXT (Japan). We thank the Research Center for Computational Science, Okazaki (Japan) for the use of their facility in our computational studies.

Abstract

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Wohin soll es gehen? Zwei verschiedene Enantiomere wurden mit einem einzigen Organokatalysator synthetisiert, je nachdem ob der Reaktion eine achirale organische Säure zugesetzt wurde oder nicht. Die Säure könnte die Orientierung des Substrats am Katalysatorzentrum verändern und so eine effiziente Chiralitätsumkehr in Aldol- und Mannich-Produkten bewirken.

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