N,N-Dimesylimides and N,N-dinosylimides as new leaving groups for the stereoselective nucleophilic substitution of amines

Article abstract of DOI:10.1016/S0957-4166(97)00229-2

The enantiospecific transformation of the optically active amines 1 and 2 via the nucleophilic substitution of the N,N-dimesylimides (1Ms, 2Ms) and the N,N-dinosylimides (1Ns, 2Ns) to the corresponding alcohols 3 and 4 is reported. Different oxygen nucleophiles were used and the alcohol products were enriched with 74-95% of the enantiomer formed by inversion of configuration.