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Highly Enantio- and Diastereoselective Reactions of γ-Substituted Butenolides Through Direct Vinylogous Conjugate Additions

Authors

  • Wen Zhang,

    1. Key Laboratory of Natural Medicine and Immune, Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 (P. R. China)
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    • These authors contributed equally to this work.

  • Davin Tan,

    1. King Abdullah University of Science and Technology (KAUST), Division of Chemical and Life Sciences & Engineering, and KAUST Catalysis Center, Thuwal, 23955-6900 (Saudi Arabia)
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    • These authors contributed equally to this work.

  • Richmond Lee,

    1. King Abdullah University of Science and Technology (KAUST), Division of Chemical and Life Sciences & Engineering, and KAUST Catalysis Center, Thuwal, 23955-6900 (Saudi Arabia)
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    • These authors contributed equally to this work.

  • Guanghu Tong,

    1. Key Laboratory of Natural Medicine and Immune, Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 (P. R. China)
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  • Wenchao Chen,

    1. Key Laboratory of Natural Medicine and Immune, Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 (P. R. China)
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  • Baojian Qi,

    1. Key Laboratory of Natural Medicine and Immune, Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 (P. R. China)
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  • Prof. Dr. Kuo-Wei Huang,

    Corresponding author
    1. King Abdullah University of Science and Technology (KAUST), Division of Chemical and Life Sciences & Engineering, and KAUST Catalysis Center, Thuwal, 23955-6900 (Saudi Arabia)
    • King Abdullah University of Science and Technology (KAUST), Division of Chemical and Life Sciences & Engineering, and KAUST Catalysis Center, Thuwal, 23955-6900 (Saudi Arabia)
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  • Prof. Dr. Choon-Hong Tan,

    Corresponding author
    1. Key Laboratory of Natural Medicine and Immune, Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 (P. R. China)
    2. Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
    • Key Laboratory of Natural Medicine and Immune, Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 (P. R. China)
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  • Prof. Dr. Zhiyong Jiang

    Corresponding author
    1. Key Laboratory of Natural Medicine and Immune, Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 (P. R. China)
    • Key Laboratory of Natural Medicine and Immune, Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 (P. R. China)
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  • This work was supported by the NSFC (21072044) and the Excellent Youth Foundation of Henan Scientific Committee (114100510003) to Z.J., and by KAUST to K.-W. H.

Abstract

original image

The strength of the weak: An L-tert-leucine-derived amine–thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state.

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