Retro-Cope eliminations in the synthesis of 1,2,5-oxadiazinanes from allylamines and nitrones: a method for the amination of unactivated alkenes

Abstract

Heating an allylamine (e.g.9) and a nitrone (e.g.10) in an inert solvent produces often excellent yields of a 1,2,5-oxadiazinane (e.g.11) by a pathway which features a retro-Cope elimination and a Meisenheimer rearrangement; reduction of the oxadiazinanes leads to vicinal diamines and hence overall amination of the alkene function in the original allylamine.