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

Beksultanova N., Gozukara Z., Araz M., Bulut M., POLAT ÇAKIR S., AYGÜN M., ...Daha Fazla

CHIRALITY, cilt.33, sa.8, ss.465-478, 2021 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 33 Sayı: 8
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1002/chir.23320
  • Dergi Adı: CHIRALITY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, BIOSIS, Biotechnology Research Abstracts, Chemical Abstracts Core, Chimica, EMBASE, MEDLINE
  • Sayfa Sayıları: ss.465-478
  • Anahtar Kelimeler: asymmetric synthesis, chiral FAM ligands, chiral metal catalyst, heteroaryl&#8208, substituted pyrrolidines, ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION, AZOMETHINE YLIDES, SELF-DISPROPORTIONATION, DERIVATIVES, ENANTIOMERS
  • Dokuz Eylül Üniversitesi Adresli: Evet

Özet

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.