A Stereoselective Access to Cyclic cis‐1,2‐Amino Alcohols from trans‐1,2‐Azido Alcohol Precursors

Abstract

Au niqueo ne-pot synthesiso fc yclic cis-1,2-aminoa lcoholsf rom trans-1,2-azido alcohol precursors wasd eveloped. Thek ey step is highlighted by the stereoselective reductiono ft he cyclic aalkoxy imines, which could be prepared from the corresponding azides by ruthenium catalysisu nder photolytic conditions.R emarkably,t his unprecedented reaction pathway offers as tereodivergent access to structurallyd iverse cyclic1 ,2-aminoa lcohols.

In situ generation of N-unsubstituted imines from alkyl azides and their applications for imine transfer via copper catalysis

“…1B). Further improvement of this scheme was reported by Park and Rhee and coworkers (31)(32)(33)(34), who accomplished the generation of N-H imines using a Ru catalyst and then trapping them with various reagents. However, they required the use of noble metal and often need light assistance.…”