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


Beksultanova N., Gözükara Z., Araz M., Bulut M., Polat-Çakır S., AYGÜN M., ...More

Chirality, vol.33, no.8, pp.465-478, 2021 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 33 Issue: 8
  • Publication Date: 2021
  • Doi Number: 10.1002/chir.23320
  • Journal Name: Chirality
  • Journal Indexes: Science Citation Index Expanded, Scopus, Academic Search Premier, Applied Science & Technology Source, BIOSIS, Biotechnology Research Abstracts, Chemical Abstracts Core, Chimica, EMBASE, MEDLINE
  • Page Numbers: pp.465-478
  • Keywords: asymmetric synthesis, chiral FAM ligands, chiral metal catalyst, heteroaryl&#8208, substituted pyrrolidines, ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION, AZOMETHINE YLIDES, SELF-DISPROPORTIONATION, DERIVATIVES, ENANTIOMERS

Abstract

© 2021 Wiley Periodicals LLC.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.