Asymmetric Diaza-Cope Rearrangement Employing α-Keto Esters

Significance

Expanding upon previous work the authors report the first diaza-Cope rearrangement employing α-keto esters. Rearrangement of diimines derived from the reaction of (R,R)-1 with aryl aldehydes and keto esters provides a highly stereospecific route to α-substituted syn-α,β-diamino ester diimines [(R,S)-2a]. The corresponding amines are interesting from both synthetic and biological perspectives.