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

Trienamin-Aktivierung wurde für die Entwicklung einer γ,δ-regioselektiven Diels-Alder-Reaktion mit elektronenarmen β-substituierten 2,4-Dienen und 2,4-Dienalen genutzt. Die resultierenden multifunktionellen Cycloaddukte enthalten perfekt positionierte funktionelle Gruppen, wodurch ein 1,5-Hydridtransfer von der C-H-Gruppe eines Aldehyds an ein aktiviertes Alken unter sequenzieller Katalyse eines Carbens ermöglicht wird (siehe Schema).

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