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Catalytic Asymmetric [8+2] Cycloaddition: Synthesis of Cycloheptatriene-Fused Pyrrole Derivatives

Authors

  • Mingsheng Xie,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)
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  • Prof. Dr. Xiaohua Liu,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)
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  • Xiaoxia Wu,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)
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  • Yunfei Cai,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)
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  • Dr. Lili Lin,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)
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  • Prof. Dr. Xiaoming Feng

    Corresponding author
    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)
    2. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China)
    • Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China)

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  • We thank the National Basic Research Program of China (973 Program: No. 2011CB808600), the National Natural Science Foundation of China (Nos. 21021001, 21290182, and 21172151) and the Ministry of Education (No. 20110181130014) for financial support.

Abstract

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Add a ring: A catalytic asymmetric [8+2] cycloaddition reaction of azaheptafulvenes with alkylidene malonates was developed. When employing catalytic amounts of a chiral N,N′-dioxide L–NiII complex, the reaction afforded functionalized cycloheptatriene-fused pyrrole derivatives in excellent yields (up to 99 %), diastereoselectivities (>95:5 d.r.), and enantioselectivities (91–97 % ee) under mild conditions.

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