FAM-Ag-catalyzed asymmetric synthesis of heteroaryl-substituted pyrrolidines

Date

2021-01-01

Author

Beksultanova, Nurzhan
Gözükara, Zeynep
Araz, Mihrimah
Bulut, Merve
Polat-Çakır, Sıdıka
AYGÜN, MUHİTTİN
Doğan, Özdemir

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New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1–4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1–4 (cyclohexyl ferrocenyl aziridinyl methanol) were synthesized to form a small ligand library and used as chiral catalysts with AgOAc for the asymmetric synthesis of heteroaryl-substituted pyrrolidines by the 1,3-dipolar cycloaddition (1,3-DC) reaction of azomethine ylides. 2-Thienyl, 2-furyl, 2-, 3-, and 4-pyridyl aldimines were prepared and used with N-methylmaleimide, dimethyl maleate, tert-butyl acrylate, methyl acrylate, and acrylonitrile to form the corresponding heteroaryl-substituted pyrrolidines. 1,3-DC reactions yielded the expected cycloadducts in up to 89% yield and up to 76% ee that could be increased up to 95% ee upon crystallization. New chiral ligands NFAM1–4 and CFAM1–4 were fully characterized, and their absolute stereochemistry was determined by single-crystal X-ray analysis.

URI

https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85106439011&origin=inward
https://hdl.handle.net/11511/90910

Journal

Chirality

DOI

https://doi.org/10.1002/chir.23320

Collections

Department of Chemistry, Article

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Citation Formats

N. Beksultanova et al., “FAM-Ag-catalyzed asymmetric synthesis of heteroaryl-substituted pyrrolidines,” Chirality, pp. 0–0, 2021, Accessed: 00, 2021. [Online]. Available: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85106439011&origin=inward.