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Chinese Journal of Organic Chemistry >

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

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

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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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

Cite this article

Wu Lizuo , Zhang Fengyuan , Zhang Zhentao , Shang Lei , Liu Yu . Ming-Phos/Copper(I)-Catalyzed Asymmetric Intermolecular[3+2] Cycloaddition of Azomethine Ylides with Trifluoromethyl Enones[J]. Chinese Journal of Organic Chemistry, 2020 , 40(8) : 2460 -2467 . DOI: 10.6023/cjoc202004038

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