Self-immolative asymmetric synthesis in the allylic rearrangement of an optically active amine oxide

Abstract

Transfer of chirality of tetraco-ordinate nitrogen to carbon atom occurred in the thermal sigmatropic rearrangement of (+)-N-trans-but-2-enyl-N-ethyl-p-toluidine oxide to (+)-O-1-methylprop-2-enyl-N-ethyl-p-tolylhydroxylamine, whose absolute configuration was correlated with (S)-(+)-butan-2-ol.