Direct catalytic enantioselective aza-Diels-Alder reactions

Abstract

(Chemical Equation Presented) Proline and its derivatives catalyze the asymmetric one-pot three-component aza-Diels-Alder reaction between unmodified α,β-unsaturated cyclic ketones, aqueous formaldehyde, and aryl amines with excellent chemo- and enantioselectivities (see scheme). Furthermore, this reaction provides a highly enantioselective entry to bicyclic non-proteogenic amino acid derivatives. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.