Meisenheimer rearrangements of N-allyl 2-azabornane derivatives

A study of the asymmetric [2,3]-Meisenheimer rearrangement of tertiary amin e-N-oxides was carried out, in order to provide a method for the preparatio n 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]-Meis enheimer 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.