Asymmetric synthesis of aryl-substituted pyrrolidines by using CFAM ligand–AgOAc chiral system via 1,3-dipolar cycloaddition reaction

Date

2023-01-01

Author

Beksultanova, Nurzhan
Doğan, Özdemir

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We have prepared a ligand library based on a ferrocenyl aziridinyl methanol core unit (simply called FAM) having a phenyl group, a cyclohexyl group, and a naphthyl group to be used in 1,3-dipolar cycloaddition (1,3-DC) reactions for the synthesis of chiral pyrrolidines. These chiral ligands were used with AgOAc in 1,3-DC reactions taking place between the aryl-substituted azomethine ylides and N-methylmaleimide as the dipolarophile. In each case, the expected aryl-substituted pyrrolidines were obtained in good to excellent yields with acceptable enantioselectivities favoring only the endo product. The chiral catalyst system CFAM4–AgOAc was also used in 1,3-DC reaction with different dipolarophiles such as dimethyl maleate, tert-butyl acrylate, methyl acrylate, trans-chalcone, and vinyl sulfone. In each case, the cycloadducts were obtained in acceptable yields albeit with low ee. Fortunately, it was possible to increase the ee up to >99% upon crystallization.

Subject Keywords

1, 3-DC reaction, chiral metal catalyst, chiral pyrrolidines, NON-BIARYL ATROPISOMERS, AZOMETHINE YLIDES, CATALYSTS, 1,3-DC reaction, chiral metal catalyst, chiral pyrrolidines

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https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85150914345&origin=inward
https://hdl.handle.net/11511/102893

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Department of Chemistry, Article