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Paper | Regular issue | Vol 100, No. 4, 2020, pp.585-599
Published online, 10th March, 2020
DOI: 10.3987/COM-20-14230
Ag(I)/sec-Amine-Amidphos-Catalyzed endo-Stereoselective Synthesis of Fully Substituted Pyrrolidines via 1,3-Dipolar Cycloaddition Based on Azomethine Ylides

Haifei Wang, Chen Zhang, Jialin Liu, Xinluo Song, and Haiyun Jiang*

*College of Packaging and Materials Engineering, Hunan University of Technology, Zhuzhou 412007, China

Abstract

Cooperative catalysis using multifunctional organic scaffolds in combination with transition-metal ions is emerging as a powerful tool in asymmetric synthesis. In this report, a series of multifunctional amidophosphanes derived from substituted 1,2-benzenediamine or 2-aminobenzylamine and chiral α-amino acids, in combination with silver(I) salts, have been developed to cooperatively catalyze the azomethine ylides-involved 1,3-dipolar cycloaddition with maleates. Under optimal conditions, fully substituted endo-pyrrolidines were obtained in high to excellent yields (up to 92% yield) and enantioselectivities (up to 94% ee).