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Chiral Primary Amine Catalyzed Enantioselective Protonation via an Enamine Intermediate

Authors

  • Niankai Fu,

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
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    • These authors contributed equally to this work.

  • Long Zhang,

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
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    • These authors contributed equally to this work.

  • Jiuyuan Li,

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
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  • Prof. Sanzhong Luo,

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
    • Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
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  • Prof. Jin-Pei Cheng

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
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  • We thank the Natural Science Foundation of China (20972163), the National Science Fund for Distinguished Young Scholars (21025208), and the National Basic Research Program of China (2011CB808600) for financial support. We also thank Prof. M. X. Wang from Tsinghua University for helpful discussions.

Abstract

original image

Ein chirales Diamin katalysiert asymmetrische Friedel-Crafts-Reaktionen über die enantioselektive Protonierung eines Enamins. Dieser Prozess verknüpft eine Reihe von α-substituierten Acroleinen und Indolen in hohen Ausbeuten und mit Enantioselektivitäten bis 94 % ee. Eine O-H/π-Wechselwirkung zwischen H2O und dem Indolring spielt im Übergangszustand eine wichtige Rolle (siehe Schema).

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