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

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.

Graphical Abstract

Keywords:

• aza-Henry reaction
• N-BOC imines
• asymmetric nitroaldol reaction
• nitroethane

Acknowledgments

We thank the Middle East Technical University (METU) for its financial support.