Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1614-1621.DOI: 10.6023/cjoc202010040 Previous Articles     Next Articles



马海a, 于广浩a, 隋峰a, 杨米一a, 刘丽a, 李慧杰a, 李峰b,*(), 赵庆贺a,*()   

  1. a 中国中医科学院中药研究所 北京 100700
    b 商丘师范学院化学化工学院 药物绿色合成河南省工程实验室 河南商丘 476000
  • 收稿日期:2020-10-29 修回日期:2020-12-05 发布日期:2020-12-24
  • 通讯作者: 李峰, 赵庆贺
  • 作者简介:
    † 共同第一作者(These authors contributed equally to this work).
  • 基金资助:

Triethylamine-Catalyzed Cascade Reaction of γ-Hydroxy-α,β-unsaturated Ketones with Trifluoromethyl Ketones via Hemiketal Intermediates

Hai Maa, Guanghao Yua, Feng Suia, Miyi Yanga, Li Liua, Huijie Lia, Feng Lib,*(), Qinghe Zhaoa,*()   

  1. a Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700
    b College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000
  • Received:2020-10-29 Revised:2020-12-05 Published:2020-12-24
  • Contact: Feng Li, Qinghe Zhao
  • About author:
    * Corresponding authors. E-mail: ;
  • Supported by:
    Voluntary Program of China Academy of Chinese Medical Sciences(ZZ0908028)

Et3N-catalyzed cascade reaction of trifluoromethyl ketones and γ-hydroxy-α,β-unsaturated ketones via hemiketal intermediate is investigated. The adducts could be easily obtained in good to excellent yields with moderate diastereoselectivities. The reaction proceeded smoothly to give the desired product in 92% yield and with 96% ee in the presence of a glycosyl and quinidine-based bifunctional chiral thiourea catalyst.

Key words: γ-hydroxy-α,β-unsaturated ketone, trifluoromethyl ketone, 1,3-dioxolanes derivative, chiral thiourea