Chinese Journal of Catalysis ›› 2016, Vol. 37 ›› Issue (4): 476-483.DOI: 10.1016/S1872-2067(15)61057-9

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Catalytic nucleophilic addition of terminal alkynes to α,β-unsaturated-γ-lactams

Maorong Wanga,b, Bao Gaoa,b, Hanmin Huanga   

  1. a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, Gansu, China;
    b University of Chinese Academy of Sciences, Beijing 100049, China
  • Received:2016-01-11 Revised:2016-01-26 Online:2016-03-30 Published:2016-03-30
  • Contact: Hanmin Huang
  • Supported by:

    This work was supported by the National Natural Science Foundation of China(21222203, 21172226, 21133011).

Abstract:

A novel catalytic reaction has been developed for the nucleophilic addition of terminal alkynes to α,β-unsaturated-γ-lactams via a cyclic N-acyliminium ion intermediate. This simple reaction proceeds rapidly under mild conditions, and provided a practical approach for the synthesis of a wide range of 5-alkynyl-2-pyrrolidinones in moderate to good yields (45%-76%).

Key words: Carbon-hydrogen addition, Brönsted acid, N-Acyliminium ion, Terminal alkyne, Pyrrolidin-2-one