4.6 Article

First Organocatalytic Asymmetric Synthesis of 1-Benzamido-1,4-Dihydropyridine Derivatives

Journal

MOLECULES
Volume 23, Issue 10, Pages -

Publisher

MDPI
DOI: 10.3390/molecules23102692

Keywords

chiral base; 1,4-dihydropyridine; enantioselective; hydrazone; organocatalysis

Funding

  1. Ministerio de Economia, Industria y Competitividad [CTQ2017-88091-P]
  2. Universidad de Zaragoza [JIUZ-2017-CIE-05]
  3. Gobierno de Aragon-Fondo Social Europeo [E07_17R]

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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 beta-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.

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