Chinese Journal of Applied Chemistry ›› 2023, Vol. 40 ›› Issue (1): 146-154.DOI: 10.19894/j.issn.1000-0518.220155

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Structurally Simplified 4-Hydroxyprolinamide for Highly Efficient Asymmetric Michael Addition of Aldehydes to Nitroolefins

Yan-Qin CHENG1, Zhuo-Xi LI1, You-Di WANG1, Juan-Juan XU1(), Zheng BIAN2()   

  1. 1.School of Pharmacy,Guangzhou Xinhua University,Guangzhou 510520,China
    2.Key Laboratory of Polyoxometalate Science of the Ministry of Education,Faculty of Chemistry,Northeast Normal University,Changchun 130024,China
  • Received:2022-04-26 Accepted:2022-08-09 Published:2023-01-01 Online:2023-01-28
  • Contact: Juan-Juan XU,Zheng BIAN
  • About
  • Supported by:
    the Characteristic Innovation Programs of Universities in Guangdong Province(2018KTSCX318)


The structurally simplified trans-4-hydroxy-L-prolinamide derivatives are prepared as the efficient organocatalysts for Michael-type asymmetric reactions. Their catalytic behaviors are evaluated in the asymmetric Michael addition of aldehydes to nitroolefins with (S)-1,1'-bi-2-naphthol as the co-catalyst. Excellent diastereo-and enantioselectivities(respectively up to >99/1 and 99%), as well as high yields(up to 96%)are achieved even at the catalyst loading of as low as 0.5%~1%(molar percent). This study provides a facile method to develop the low-cost and highly efficient organocatalyst system for the asymmetric Michael addition reactions.

Key words: Asymmetric catalysis, 4-Hydroxy-L-prolinamide, S)-1, 1'-Bi-2-naphthol, Michael addition

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