Enantioselective Cyclopropanation of 4‐Nitroisoxazole Derivatives

Abstract

AbstractThe present study reports an asymmetric organocatalytic cascade reaction of 4‐nitroisoxazole derivative with α,β‐unsaturated aldehydes catalysed by chiral secondary amine. Using this approach, 1,2,3‐trisubstituted cyclopropane products were obtained in isolated yields up to 98% with moderate diastereoselectivities, and enantiopurity up to 99% ee. Moreover, this synthetic protocol can be used for further applications, as shown by a set of additional transformations of the corresponding cyclopropanes and by the formal synthesis of GABA ligands.magnified image