Stereoselective Synthesis of Protected Amines and Diamines from Alkenes using N,N-Dichloro-t-butylcarbamate

Article abstract of DOI:10.1016/0040-4039(91)80624-F

N,N-Dichloro-t-butylcarbamate (1) reacts with alkenes (2) in a regio- and stereo-selective manner to give the trans-chlorocarbamate adducts (3).Treatment of (3) with base gives aziridines (5), and reaction of (3) and (5) with sodium azide leads selectively to the versatile diamine precursors (6) and (7).In situ reduction of (3) with Zn/NH4OAc leads directly to Boc-protected amines (10).