Asymmetric imine isomerisation in the enantioselective synthesis of chiral amines from prochiral ketones

Article abstract of DOI:10.1016/0040-4039(95)00641-O

An asymmetric catalytic synthesis of chiral amines using a chiral base catalysed [1,3]-proton shift reaction of imines is described. The isomerisation reaction of N-benzylimines 2a-b derived from prochiral ketones (benzylacetone, acetophenone) and p-substituted benzylamines, is catalysed by chiral alcohols and aminoalcohols 5-12 and gives enantiomerically enriched (up to 44% e.e.) N-benzylidene derivatives 3a-b. The resulting products 3a-b are readily hydrolysed to their corresponding amines 4a-b.