Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2904-2911.DOI: 10.6023/cjoc202005037 Previous Articles     Next Articles


张璐a, 刘爱芹c, 刘华铮a, 万仁忠a, 孙书涛b, 刘磊b   

  1. a 山东农业大学动物科技学院 山东泰安 271018;
    b 山东大学化学与化工学院 济南 250100;
    c 山东第一医科大学(山东省医学科学院)药物研究所 济南 250062
  • 收稿日期:2020-05-15 修回日期:2020-06-03 发布日期:2020-06-13
  • 通讯作者: 万仁忠, 孙书涛, 刘磊;;
  • 基金资助:

Catalytic Asymmetric Synthesis of β,γ-Alkynyl α-Amino Esters via Chemo- and Enantio-selective Transfer Hydrogenation

Zhang Lua, Liu Aiqinc, Liu Huazhenga, Wan Renzhonga, Sun Shutaob, Liu Leib   

  1. a College of Animal Science and Veterinary Medicine, Shandong Agricultural University, Taian, Shandong 271018;
    b School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100;
    c Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250062
  • Received:2020-05-15 Revised:2020-06-03 Published:2020-06-13
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21722204, 21971148).

An effective chemo- and enantioselective transfer hydrogenation of β,γ-alkynyl α-imino esters to prepare optically pure β,γ-alkynyl α-amino esters has been described. The excellent chemoselectivity was achieved by using chiral phosphoric acid catalyzed asymmetric reduction with benzothiazoline as hydride donor. The reaction exhibited good functional group tolerance, providing a range of optically active non-natural amino esters with excellent enantioselectivity.

Key words: β,γ-alkynyl α-amino ester, chemoselectivity, enantioselectivity, transfer hydrogenation, benzothiazoline