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Catalytic Asymmetric Aziridination of α,β-Unsaturated Aldehydes
L. Deiana, P. Dziedzic, G.-L. Zhao, J. Vesely, I. Ibrahem, R. Rios, J. Sun, A. Córdova*
Stockholm University and Mid Sweden University, Sundsvall, Sweden
20 July 2011 (online)
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.