T. Fukuyama, Mui Cheung, T. Kan
Aug 1, 1999
Citations
0
Influential Citations
62
Citations
Journal
Synlett
Abstract
: N-Carboalkoxy-2-nitrobenzenesulfonamides, readily prepared by acylation of 2-nitrobenzenesulfonamide ( o -NsNH 2 ), can be alkylated by either conventional or Mitsunobu protocols. Since the o-nosyl group can be deprotected under mild conditions, a variety of N-carboalkoxy derivatives of primary amines may be prepared in excellent yields from the corresponding alcohols and/or halides. In addition, allyloxycarbonyl (Alloc), t -butoxycarbonyl ( t - Boc), and benzyloxycarbonyl (Cbz) groups can be deprotected in the presence of the o-nosyl group, allowing the resultant N- alkylated 2-nitrobenzenesulfonamides to be used for further preparation of secondary amines.