Mechanistic and stereochemical aspects of the Lewis acid mediated cleavage of α-aminoacetals

The TMSOTf mediated nucleophilic cleavage of α-aminoacetals can be used to prepare a variety of substituted amines, with variable levels of stereocontrol depending on the substitution patterns. The reaction most likely proceeds via either an α-alkoxy aziridinium ion or an α-oxocarbenium ion depending on the type of nucleophile.