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Versatile Enantioselective [3+2] Cyclization between Imines and Allenoates Catalyzed by Dipeptide-Based Phosphines

Authors

  • 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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  • 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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  • Prof. Dr. Youqing Wang,

    1. Provincial Key Laboratory of Natural Medicine and Immuno-Engineering, Henan University, Jinming Campus, Kaifeng, Henan, 475004 (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 (R-143-000-469-112) for generous financial support.

Abstract

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Ohne Umschweife: Die Titelreaktion gelingt mit 5 Mol-% des Katalysators 1 und ist binnen 1 h abgeschlossen. Die 2-Alkyl- und 2-Aryl-substituierten 3-Pyrroline werden in guten Ausbeuten und mit hoher Enantioselektivität erhalten. Die Anwendung der Methode in einer kurzen formalen Synthese von (+)-Trachelanthamidin wird ebenfalls gezeigt. Boc=tert-Butoxycarbonyl, M.S.=Molekularsieb, TBDPS=tert-Butyldiphenylsilyl.

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