Asymmetric aza-Henry reaction of BOC-protected imines with zinc-FAM catalyst

Beksultanova N., DOĞAN Ö.

Synthetic Communications, vol.54, no.5, pp.371-378, 2024 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 54 Issue: 5
  • Publication Date: 2024
  • Doi Number: 10.1080/00397911.2024.2303054
  • Journal Name: Synthetic Communications
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica
  • Page Numbers: pp.371-378
  • Keywords: asymmetric nitroaldol reaction, aza-Henry reaction, N-BOC imines, nitroethane
  • Middle East Technical University Affiliated: Yes

Abstract

Derivatives of ferrocenyl-substituted aziridinyl methanol (FAM) ligands were used with zinc metal for asymmetric aza-Henry (nitro-aldol) reaction of N-Boc protected imines with nitroalkanes. At optimized reaction conditions Zn-PFAM1 catalyst system with a variety of aromatic imines provided products in up to 77% ee and 88% yield. In addition, the reaction of N-Boc substituted imines with nitroethane also proceeded smoothly with moderate enantioselectivities and diastereoselectivities.