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Multistep One-Pot Synthesis of Enantioenriched Polysubstituted Cyclopenta[b]indoles

Authors

  • Biao Xu,

    1. Education Ministry Key Laboratory on Luminescence and Real-Time Analysis, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715 (China)
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  • Zhi-Lei Guo,

    1. Education Ministry Key Laboratory on Luminescence and Real-Time Analysis, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715 (China)
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  • Wan-Yan Jin,

    1. Education Ministry Key Laboratory on Luminescence and Real-Time Analysis, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715 (China)
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  • Zhi-Ping Wang,

    1. Education Ministry Key Laboratory on Luminescence and Real-Time Analysis, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715 (China)
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  • Prof. Yun-Gui Peng,

    1. Education Ministry Key Laboratory on Luminescence and Real-Time Analysis, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715 (China)
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  • Prof. Qi-Xiang Guo

    Corresponding author
    1. Education Ministry Key Laboratory on Luminescence and Real-Time Analysis, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715 (China)
    • Education Ministry Key Laboratory on Luminescence and Real-Time Analysis, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715 (China)
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  • We are grateful for financial support from the NSFC (20902074) and the Fundamental Research Funds for the Central Universities (XDJK2011C054).

Abstract

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Simple steps, complex result: Consecutive organo-catalyzed reactions of 3-indolylmethanol compounds with aldehydes and N-protected indoles lead to the formation of structurally complex cyclopenta[b]indoles (see scheme, Bn=benzyl). These one-pot multistep reactions have a broad substrate scope and give the products in high yields, and with excellent diastereoselectivities and enantioselectivities.

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