Abstract
Two different methods to obtain enantiomerically pure N-alkyl and N-aryl α-sulfinyl ketimines are reported. Reaction of enantiomerically pure α-sulfinyl ketones ( 1– 6) with benzylamine or p-methoxyaniline, in the presence of molecular sieves (3 Å), yields the corresponding of N-benzyl and N- p-methoxyphenyl ketimines ( 7A– 12A and 7B– 12B). Better results were achieved by α-sulfinylation of ketimines ( 13A– 18A and 13B– 18B) with (−)-menthyl p-toluenesulfinate in the presence of lithium ( N-arylimines) or magnesium ( N-benzylimines) bases. The different tautomeric behaviour of the obtained N-aryl and N-alkyl derivatives is reported.
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