Citation: 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 shu

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

College of Chemistry and Life Science, Advanced Institute of Materials Science, Changchun University of Technology, Changchun, Jilin 130012

Corresponding author: Shang Lei, shanglei@ccut.edu.cn Liu Yu, yuliu@ccut.edu.cn
Received Date: 25 April 2020
Revised Date: 29 April 2020
Available Online: 25 May 2020
Fund Project: 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)the Science and Technology Development Project of Jilin Province 20170520137JHthe National Natural Science Foundation of China for Youth 21602015

Figures(2)

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.
- copper catalysis,
- trifluoromethyl,
- cycloaddition,
- enantioselectivity,
- ylides
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