Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1499-1509.DOI: 10.6023/cjoc202209034 Previous Articles     Next Articles



刘洋a,b, 黄翔b,c, 王敏a,b,*(), 廖建a,b,c,*()   

  1. a 中国科学院成都生物研究所 成都 610041
    b 中国科学院大学 北京 100049
    c 中国科学院成都有机化学研究所 成都 610041
  • 收稿日期:2022-09-28 修回日期:2022-11-14 发布日期:2022-12-07
  • 通讯作者: 王敏, 廖建
  • 基金资助:
    中国科学院青年创新促进会(2022375); 国家自然科学基金(21871251); 国家自然科学基金(22171258); 中国科学院生物资源(KFJ-BRP-008)

Enantioselective Copper-Catalyzed Mannich-Type Reaction of Cycic Ketimines and β,γ-Unsaturated N-Acylpyrazoles

Yang Liua,b, Xiang Huangb,c, Min Wanga,b(), Jian Liaoa,b,c()   

  1. a Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041
    b University of Chinese Academy of Sciences, Beijing 100049
    c Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041
  • Received:2022-09-28 Revised:2022-11-14 Published:2022-12-07
  • Contact: Min Wang, Jian Liao
  • Supported by:
    Youth Innovation Promotion Association of Chinese Academy of Sciences(2022375); National Natural Science Foundation of China(21871251); National Natural Science Foundation of China(22171258); Biological Resources Program, Chinese Academy of Sciences(KFJ-BRP-008)

Chiral benzosultams are an important category of bioactive compounds and functional organic molecules. Therefore, great efforts have been devoted for developing efficient methods for their preparation. A copper-catalyzed direct asymmetric Mannich-type reaction of cyclic N-sulfonyl α-iminoesters with β,γ-unsaturated N-acylpyrazoles was developed. Under mild conditions, γ-adducts were delivered in good yields with excellent regio- (γ/α>20/1), diastereoselectivities (dr>20/1) and high enantioselectivities (up to 93% ee). This method, with wide substrate-scopes and good functional group compatibility, provides potentiality for the synthesis of structurally diverse chiral benzosultam derivatives.

Key words: copper catalysis, chiral cyclic benzosulfonamide, asymmetric Mannich reaction, γ-adducts