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exo-Selective Asymmetric Diels–Alder Reaction of 2,4-Dienals and Nitroalkenes by Trienamine Catalysis

Authors

  • Zhi-Jun Jia,

    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)
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  • Quan 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)
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  • Qing-Qing 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)
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  • Peng-Qiao Chen,

    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)
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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)
    2. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041(China)
    • 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)
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  • We are grateful for financial support from the NSFC (20972101 and 21021001) and the National Basic Research Program of China (973 Program, 2010CB833300).

Abstract

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Raising the HOMO: 2,4-Dienals can react with nitroalkenes in trienamine-catalyzed asymmetric Diels–Alder reactions (see scheme). Crucial for the success is raising the HOMO energy of the diene through the introduction of appropriate substituents. The reaction exhibits unusually high enantioselectivity and exo selectivity; endo addition is possibly disfavored because of the electrostatic repulsion shown in the scheme.

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