Preparation of chiral thioureas, ureas and guanidines from (S)-2-(N,N-dialkylaminomethyl)pyrrolidines

The reaction of commercially available heterocumulenes (isothiocyanates, isocyanatobenzene, N,N'-isopropylcarbodiimide) with lithiated chiral diamines 4 provided a novel class of chiral thioureas 8, areas 9 and guanidines 10, which were isolated in good to excellent yields (60-96%). The molecular structures of compounds 8-10, derived from (S)-2-(N,N-dialkylaminotnethyl)-pyrrolidines 1-3, were determined. (C) 2004 Elsevier Ltd. All rights reserved.