Nucleophilic Substitution of Chiral Amine N,N-Ditosylderivatives

Article abstract of DOI:10.1016/S0957-4166(00)86241-2

The chiral transformation of the optically active amine 10 to the corresponding alcohol 2 with opposite configuration is reported.The transformation is carried out via an S_N2 type reaction of the N,N-ditosylimide, -NTs2, by nucleophilic attack of the hydroxide, acetate or benzoate ion to give an inversion degree of 85-100percent. 0-34percent stereoselectivity was obtained in the corresponding chloride nucleophilic substitutions.Separation parameters for the chromatographic enantioseparations of the amines 10-12, the chlorides 4, 7, 9 and the alcohol 2 using a chemically bonded cyclodextrin GLC column are discussed.