First organocatalytic asymmetric synthesis of 1-benzamido-1,4-dihydropyridine derivatives

This article belongs to the Special Issue Stereogenic Centers.Preliminary results concerning the first asymmetric synthesis of highly functionalized 1-benzamido-1,4-dihydropyridine derivatives via the reaction of hydrazones with alkylidenemalononitriles in the presence of β-isocupreidine catalyst are reported. The moderate, but promising, enantioselectivity observed (40–54% ee), opens the door to a new area of research for the asymmetric construction of new chiral 1,4-dihydropyridine derivatives, whose enantioselective catalytic preparation are still very limited. Moreover, the use of hydrazones for the enantioselective construction of chiral 1,4-dihydropyridines has been overlooked in the literature so far. Therefore, our research represents a pivotal example in this field which remains still unexplored.This research was funded by Ministerio de Economía, Industria y Competitividad [CTQ2017-88091-P], Universidad de Zaragoza [JIUZ-2017-CIE-05] and Gobierno de Aragón-Fondo Social Europeo [Research Group E07_17R].Peer reviewe