Get access

Trienamines Derived from Interrupted Cyclic 2,5-Dienones: Remote δ,ε-C[DOUBLE BOND]C Bond Activation for Asymmetric Inverse-Electron-Demand Aza-Diels–Alder Reaction

Authors

  • Xin Feng,

    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)
    Search for more papers by this author
    • These authors contributed equally to this work.

  • Zhi 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)
    Search for more papers by this author
    • These authors contributed equally to this work.

  • 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)
    Search for more papers by this author
  • Xiang Yin,

    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)
    Search for more papers by this author
  • Prof. Dr. Rui Li,

    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)
    • 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)

    Search for more papers by this author
  • 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)
    Search for more papers by this author
  • 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)

    Search for more papers by this author

  • We are grateful for financial support from the NSFC (21125206, 21021001 and 21372160) and the National Basic Research Program of China (973 Program, 2010CB833300).

Abstract

original image

Newly framed: The δ,ε C[DOUBLE BOND]C bond of an interrupted cyclic 2,5-dienone induces the formation of a linear trienamine in the presence of a chiral primary amine, thus enabling the δ,ε-C[DOUBLE BOND]C bond to participate in a highly asymmetric inverse-electron-demand aza-Diels–Alder (DA) reaction with electron-deficient 1-azadienes. The DA reaction can be coupled with a Michael addition to produce a polycyclic framework with complete stereocontrol.

Ancillary