Asymmetric aza-Diels–Alder and Cation–olefin Cyclization Sequence: a Concise Way to Fused Chiral Cyclopenta[b]piperidines

Authors

  • Qing-Zhu Li,

    1. Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28-85502609
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  • Lei Ma,

    1. Centre for Drug Evaluation, State Food and Drug Administration, Beijing 100038 (China)
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  • Dr. Lin Dong,

    1. Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28-85502609
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  • Prof. Dr. Ying-Chun Chen

    Corresponding author
    1. Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28-85502609
    • Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86) 28-85502609
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Abstract

An asymmetric aza-Diels–Alder and cation–olefin cyclization sequence has been developed to construct cyclopenta[b]piperidine skeletons with moderate yields and excellent stereoselectivities, by employing 5-enals and N-Ts-1-aza-1,3-butadienes as the starting materials. A designed domino cation–olefin/Friedel–Crafts reaction verified that the cyclization of N-Ts iminium ion underwent a stepwise cationic process.

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