Synthesis and studies on gem-fluorinated 2-azabicyclo[n.1.0]alkanes

Three novel amines all possessing gem-difluorocyclopropane, secondary amino group and a fused aliphatic cycle were synthesized by difluorocyclopropanation of N-Boc protected enamides. The compounds were stable when amino group was blocked by protonation or acylation, but otherwise underwent fragmentation already at the room temperature. Chemical structure, physico-chemical properties and fragmentation mechanisms of the fluorinated amines are studied in details.