Addition reaction of O-toluamides with chiral auxiliary derived from 2-amino-1,3-propanediols to imines

Stereoselectivity of the addition reaction of o-toluamides, incorporating 2-amino-1,3-propanediols as chiral auxiliary to imines has been studied. Addition products, diastercomerically enriched, after column chromatography separation were obtained and further transformed to (S)-(-)-or (R)-(+)-8-oxoberbines with ee up to 97%.