Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2460-2467.DOI: 10.6023/cjoc202004038 Previous Articles     Next Articles

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   

  1. 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 出版日期:2020-08-25 发布日期:2020-05-28
  • 通讯作者: 刘宇, 尚垒 E-mail:yuliu@ccut.edu.cn;shanglei@ccut.edu.cn
  • 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.

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   

  1. College of Chemistry and Life Science, Advanced Institute of Materials Science, Changchun University of Technology, Changchun, Jilin 130012
  • Received:2020-04-25 Revised:2020-04-29 Online:2020-08-25 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).

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