Highly Enantioselective [3+2] Annulation of Morita–Baylis–Hillman Adducts Mediated by L-Threonine-Derived Phosphines: Synthesis of 3-Spirocyclopentene-2-oxindoles having Two Contiguous Quaternary Centers

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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  • 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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  • 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 and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) for generous financial support.

Abstract

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Spiralbindung: Morita–Baylis-Hillman-Addukte wurden als C3-Bausteine in der asymmetrischen [3+2]-Anellierung mit Malonitrilsubstraten in Gegenwart des L-Threoninderivats 1 als Katalysator eingesetzt. Die Reaktion ist hoch regio- und stereoselektiv und liefert optisch angereicherte 3-Spirocyclopenten-2-oxindole mit zwei aufeinander folgenden quartären Zentren. Boc=tert-Butoxycarbonyl, PMB=para-Methoxybenzyl, TIPS=Triisopropylsilyl.

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