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2020 , Vol. 40 >Issue 8: 2460 - 2467

DOI: https://doi.org/10.6023/cjoc202004038

研究论文

Ming-Phos/铜催化的甲亚胺叶立德与三氟甲基烯酮的不对称[3+2]环加成反应

  • 武力左 ,
  • 张峰源 ,
  • 章振涛 ,
  • 尚垒 ,
  • 刘宇
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  • 长春工业大学化学与生命科学学院 材料科学高等研究院 吉林长春 130012

收稿日期: 2020-04-25

  修回日期: 2020-04-29

  网络出版日期: 2020-05-28

基金资助

吉林省科技发展计划（No.20170520137JH）和国家自然科学基金青年基金（No.21602015）资助项目.

收起

Ming-Phos/Copper(I)-Catalyzed Asymmetric Intermolecular[3+2] Cycloaddition of Azomethine Ylides with Trifluoromethyl Enones

  • Wu Lizuo ,
  • Zhang Fengyuan ,
  • Zhang Zhentao ,
  • Shang Lei ,
  • Liu Yu
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  • College of Chemistry and Life Science, Advanced Institute of Materials Science, Changchun University of Technology, Changchun, Jilin 130012

Received date: 2020-04-25

  Revised date: 2020-04-29

  Online published: 2020-05-28

Supported by

Project supported by the Science and Technology Development Project of Jilin Province (No. 20170520137JH) and the National Natural Science Foundation of China for Youth (No. 21602015).

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摘要

含有三氟甲基的手性吡咯烷骨架是许多天然产物和药物的重要中间体，其高效的不对称合成方法是有机化学研究热点之一.通过Ming-Phos手性配体实现了铜催化的甲亚胺叶立德与β-三氟甲基-α，β-不饱和酮的不对称[3+2]环加成反应，以较高的产率和对映选择性合成了一系列含三氟甲基的手性吡咯烷化合物（ee值高达98%，产率高达99%）.该方法条件温和，操作简单，配体简单易得，且具有良好的底物普适性和官能团兼容性.

关键词： 铜催化; 三氟甲基; 环加成; 不对称催化; 叶立德

本文引用格式

武力左 , 张峰源 , 章振涛 , 尚垒 , 刘宇 . Ming-Phos/铜催化的甲亚胺叶立德与三氟甲基烯酮的不对称[3+2]环加成反应[J]. 有机化学, 2020 , 40(8) : 2460 -2467 . DOI: 10.6023/cjoc202004038

Abstract

Chiral pyrrolidine skeletons containing trifluoromethyl group are core structural motifs in many natural products and medicines. As a consequence, extensive studies have been conducted on the exploitation of efficient methods for the asymmetric synthesis of such compounds. In this paper, Ming-Phos/Cu(I)-catalyzed asymmetric intermolecular[3+2] cycloaddition reaction of azomethine ylides and β-trifluoromethyl-α,β-unsaturated ketone was reported. A broad substrate scope was observed with high yield and enantioselectivity (up to 99% yield and 98% ee). The method is featured by its mild conditions, simple operation, easily available ligands and good functional group compatibility.

Key words： copper catalysis; trifluoromethyl; cycloaddition; enantioselectivity; ylides

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