A Concise Assembly of Electron-Deficient 2,4-Dienes and 2,4-Dienals: Regio- and Stereoselective exo-Diels–Alder and Redox Reactions through Sequential Amine and Carbene Catalysis

Authors

  • Chao Ma,

    1. Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041 (China)
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  • Zhi-Jun Jia,

    1. Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041 (China)
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  • Jing-Xin Liu,

    1. Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041 (China)
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  • Qing-Qing Zhou,

    1. Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041 (China)
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  • Dr. Lin Dong,

    1. Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, 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 Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041 (China)
    2. College of Pharmacy, Third Military Medical University, Chongqing, 400038 (China)
    • Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041 (China)
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  • We are grateful for financial support from the NSFC (20972101, 21125206 and 21021001), and the National Basic Research Program of China (973 Program, 2010CB833300).

Abstract

original image

Ideal relay catalysis: A γ,δ-regioselective anomalous exo-Diels–Alder reaction with electron-deficient β-substituted 2,4-dienes and 2,4-dienals has been developed by using trienamine activation. The resulting multifunctional cycloadducts contain perfectly positioned functional groups, thereby facilitating a 1,5-hydride transfer from the C–H group of an aldehyde to an activated alkene under sequential catalysis of a carbene (see scheme).

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