FAM-Ag-catalyzed asymmetric synthesis of heteroaryl-substituted pyrrolidines
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CitationBeksultanova, N., Gözükara, Z., Araz, M., Bulut, M., Polat‐Çakır, S., Aygün, M., & Dogan, Ö. (2021). FAM‐Ag‐catalyzed asymmetric synthesis of heteroaryl‐substituted pyrrolidines. Chirality, 33(8), 465–478. https://doi.org/10.1002/chir.23320
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.