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Chiral Phosphine Catalyzed Asymmetric Michael Addition of Oxindoles

Authors

  • Fangrui Zhong,

    1. Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
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  • Xiaowei Dou,

    1. Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
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  • Xiaoyu Han,

    1. Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
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  • Weijun Yao,

    1. Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
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  • Qiang Zhu,

    1. Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
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  • Prof. Dr. Yuezhong Meng,

    1. State Key Laboratory of Optoelectronic Materials and Technologies and the Key Laboratory of Low-Carbon Chemistry & Energy Conservation of Guangdong Province, Sun Yat-Sen University, Guangzhou 510275 (China)
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  • Prof. Dr. Yixin Lu

    Corresponding author
    1. Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
    • Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
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  • We thank the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112), the Singapore-Peking-Oxford Research Enterprise (COY-15-EWI-RCFSA/N197-1), and GSK-EDB (R-143-000-491-592) for generous financial support.

Abstract

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Bifunctional phosphines derived from amino acids mediate the asymmetric Michael addition of 3-substituted oxindoles to activated alkenes (see scheme). Biologically relevant chiral 3,3-disubstituted oxindoles were thus prepared in high yields and with excellent enantioselectivities from 3-aryl- and 3-alkyl-substituted oxindoles and various activated alkenes.

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