Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (7): 758-763.DOI: 10.11944/j.issn.1000-0518.2019.07.180340

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Organocatalyzed Asymmetric Mannich Reaction of Isocyanoacetate with Tosylimines

WANG Liming,MU Hongwen,LU Dongze,LI Xuetao,LI Tong,JIN Ying()   

  1. Department of Pharmacy,Jilin Medical University,Jilin,Jilin 132013,China
  • Received:2018-10-29 Accepted:2019-03-06 Published:2019-07-01 Online:2019-07-02
  • Contact: JIN Ying
  • Supported by:
    Supported by the National Natural Science Foundation of China(No.21102055), the Natural Science Foundation of Jilin Province(No.20190201077JC), the Health Department of Jilin Province(No.2017J104), and the Students Program for Innovation and Entrepreneurship Training of Jilin Province(No.201817)

Abstract:

Cinchona alkaloid derivatives as organocatalysts were applied in asymmetric Mannich reaction of isocyanoacetate with N-tosyl aryl aldimines. The effect of solvent, temperature and catalyst loading ammount were investigated. The optimized conditions were confirmed to include toluene as the solvent with a molar fraction 10% loading of catalyst 1b at room temperature. The desired products were obtained in 55%~80% yield with high diastereo- and enantioselectivities(trans/cis up to >99:1 and 82%ee).

Key words: cinchona alkaloid derivatives, organocatalysis, asymmetric mannich reaction, isocyanoacetate