高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (10): 2272-2278.doi: 10.7503/cjcu20200179

• 研究论文 • 上一篇    下一篇

不对称有机催化MBH碳酸酯与噻唑基烯酮的[1+4]环化反应构建含有噻唑骨架的手性二氢呋喃衍生物

刘畅1, 张鹏飞1, 李鹏飞1,2   

  1. 1.南方科技大学理学院化学系, 深圳 518055
    2.华南理工大学广东省功能分子工程重点实验室, 广州 510006
  • 收稿日期:2020-04-03 出版日期:2020-10-10 发布日期:2020-04-15
  • 基金资助:
    国家自然科学基金(21871128);广东省功能分子工程重点实验室开放基金项目(2018kf01)

Asymmetric Organocatalytic Enantioselective [1+4]-Annulation of Morita-Baylis-Hillman Carbonates with Thiazolyl Enones for Assembling of Dihydrofurans Featuring Thiazole Skeleton

LIU Chang1, ZHANG Pengfei1, LI Pengfei1,2()   

  1. 1.Department of Chemistry,College of Science,Southern University of Science and Technology,Shenzhen 518055,China
    2.Key Lab of Functional Molecular Engineering of Guangdong Province,South China University of Technology,Guangzhou 510006,China
  • Received:2020-04-03 Online:2020-10-10 Published:2020-04-15
  • Contact: LI Pengfei E-mail:lipf@sustech.edu.cn
  • Supported by:
    This paper is supported by the National Natural Science Foundation of China(No.21871128) and the Open Fund of the Key Laboratory of Functional Molecular Engineering of Guangdong Province, China(No.2018kf01).

摘要:

发展了一种手性有机膦催化的Morita-Baylis-Hillman(MBH)碳酸酯与1-芳基-3-(5-噻唑基)-2-丙烯-1-酮的不对称[1+4]环化反应, 用于不对称合成含有噻唑骨架的手性二氢呋喃衍生物. 该反应的产率为49%~96%, 对映选择性(e.e.)为92%~99%, 非对映选择性(d.r.)从6∶1至高于20∶1. 该研究拓展了手性有机膦催化体系的应用范围, 同时为高效构建含有噻唑和二氢呋喃2种结构单元的手性杂环化合物提供了良好的催化策略.

关键词: 不对称有机催化, 环化反应, 噻唑基烯酮, MBH碳酸酯, 二氢呋喃

Abstract:

The phosphine catalyzed enantioselective [1+4]-annulation of 1-aryl-3-(thiazol-5-yl)prop-2-enone with Morita-Baylis-Hillman carbonate was developed, which enabled the formation of structurally diversified 2,3-dihydrofurans featuring thiazole skeleton in yields of 49%—96% with e.e. of 92%—99% and d.r. from 6∶1 to more than 20∶1. Notably, this work extended the application range of the established catalytic system and provided an excess to the chiral complex heterocyclic compounds containing dihydrofuran and thiazole structural units.

Key words: Asymmetric organocatalysis, Annulation, Thiazolyl enone, MBH carbonate, dihydrofuran

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