Azasugar analogues: conformationally restricted vicinal diamine derived from (S)-(-)-pyroglutamic acid

The preparation of a diamino substituted pyrrolidinone system in a diastere oselectively controlled manner is described. The procedure employed made us e of electrophilic amination of a chiral bicyclic gamma-lactam, which when subjected to sequential deprotection provided a simple route to a 3,4-diami nopyroglutaminol. The chemo selective deprotection of the amino functionali ty was also shown to be possible under mild hydrogenolytic conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.