Studies into the asymmetric Meisenheimer rearrangement

Oxidation of a variety of N-allyl prolinol derivatives gave amine N-oxides with complete diastereoselectivity. On warming, these amine N-oxides undergo [2,3]-Meisenheimer rearrangement to give O-allyl hydroxylamines, albeit with low diastereoselectivity. Attempts to promote asymmetric N-oxidation of N-allyl tertiary amines with a variety of asymmetric oxidants produced only racemic N-oxides.