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Organocatalytic Asymmetric Inverse-Electron-Demand Diels–Alder Reaction of Electron-Deficient Dienes and Crotonaldehyde

Authors

  • Jun-Long 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) 28-8550-2609
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  • Tai-Ran Kang,

    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) 28-8550-2609
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  • Si-Li Zhou,

    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) 28-8550-2609
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  • Rui Li Dr.,

    1. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041(China)
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  • Li Wu,

    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) 28-8550-2609
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  • Ying-Chun Chen Prof. Dr.

    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) 28-8550-2609
    2. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041(China)
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  • We are grateful for the financial support from the NSFC (no. 20972101), the PCSIRTC (no. IRT0846), and the National Basic Research Program of China (973 Program; no. 2010CB833300).

Abstract

original image

Another pathway for enals: The excellent β,γ-regioselectivity shown in the title reaction under dienamine catalysis efficiently gave highly diastereo- and enantioenriched cyclohexene derivatives with substantial substitution diversity (see scheme; EWG=electron-withdrawing group, TMS=trimethylsilyl).

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