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2021 , Vol. 41 >Issue 4: 1614 - 1621

DOI: https://doi.org/10.6023/cjoc202010040

研究论文

三乙胺催化的γ-羟基-α,β-不饱和酮与三氟甲基酮通过半缩酮中间体的级联反应

  • 马海 ,
  • 于广浩 ,
  • 隋峰 ,
  • 杨米一 ,
  • 刘丽 ,
  • 李慧杰 ,
  • 李峰 ,
  • 赵庆贺
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  • 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
† 共同第一作者(These authors contributed equally to this work).

收稿日期: 2020-10-29

  修回日期: 2020-12-05

  网络出版日期: 2020-12-24

基金资助

中国中医科学院自主研发(ZZ0908028)

收起

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

  • Hai Ma ,
  • Guanghao Yu ,
  • Feng Sui ,
  • Miyi Yang ,
  • Li Liu ,
  • Huijie Li ,
  • Feng Li ,
  • Qinghe Zhao
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  • 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
* Corresponding authors. E-mail: ;
E-mail:

Received date: 2020-10-29

  Revised date: 2020-12-05

  Online published: 2020-12-24

Supported by

Voluntary Program of China Academy of Chinese Medical Sciences(ZZ0908028)

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摘要

研究了三乙胺催化的γ-羟基-α,β-不饱和酮与三氟甲基酮通过半缩酮中间体的级联反应, 以高收率以及适中的非对映选择性得到了一系列产物. 在手性奎宁衍生的双功能硫脲催化剂存在下, 该反应以92%的收率以及96%的立体选择性得到目标产物.

关键词： γ-羟基-α,β-不饱和酮; 三氟甲基酮; 1,3-二噁烷衍生物; 手性硫脲

本文引用格式

马海 , 于广浩 , 隋峰 , 杨米一 , 刘丽 , 李慧杰 , 李峰 , 赵庆贺 . 三乙胺催化的γ-羟基-α,β-不饱和酮与三氟甲基酮通过半缩酮中间体的级联反应[J]. 有机化学, 2021 , 41(4) : 1614 -1621 . DOI: 10.6023/cjoc202010040

Abstract

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

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