SYNTHESIS OF ENANTIOMERICALLY PURE ACYCLIC ALPHA-SULFINYL KETIMINES

Two different methods to obtain enantiomerically pure N-alkyl and N-ar yl alpha-sulfinyl ketimines are reported. Reaction of enantiomerically pure alpha-sulfinyl ketones (1-6) with benzylamine or p-methoxyanilin e, in the presence of molecular sieves (3 Angstrom), yields the corres ponding of N-benzyl and N-p-methoxyphenyl ketimines (7A-12A and 7B-12B ). Better results were achieved by alpha-sulfinylation of ketimines (1 3A-18A and 13B-18B) with (-)-menthyl p-toluenesulfinate in the presenc e of lithium (N-arylimines) or magnesium (N-benzylimines) bases. The d ifferent tautomeric behaviour of the obtained N-aryl and N-alkyl deriv atives is reported. (C) 1998 Published by Elsevier Science Ltd. All ri ghts reserved.