Catalytic Asymmetric Aziridination of α,β-Unsaturated Aldehydes

Significance

In this full paper Córdova and coworkers compile their previous results on the catalytic asymmetric aziridination of β- (Angew. Chem. Int. Ed. 2007, 46, 778) and α-substituted (Adv. Synth. Catal. 2010, 352, 3201) α,β-unsaturated aldehydes, respectively. In addition to these results a broadened substrate scope and further functionalizations of the obtained aziridines are presented. Valuable building blocks such as N-protected β-amino esters, β-carboxyl aziridines and N-protected α-hydroxy β-amino acetals were obtained in moderate to good yields and excellent enantioselectivities. Finally proposed mechanisms for the aziridination and the NHC-catalyzed ring-opening-oxidation reactions are discussed.