Meisenheimer rearrangements of N-allyl 2-azabornane derivatives

Abstract

A study of the asymmetric [2,3]-Meisenheimer rearrangement of tertiary amine-N-oxides was carried out, in order to provide a method for the preparation of chiral allylic alcohols. The use of 2-azabornane as a chiral auxiliary gives rise to chiral tertiary amine-N-oxides, which undergo the [2,3]-Meisenheimer rearrangement with high levels of stereoselectivity. Reductive N,O-bond cleavage, mediated by ultrasound, of the O-allyl-hydroxylamine allows access to the chiral allylic alcohol.