First organocatalytic asymmetric synthesis of 1-Benzamido-1, 4-Dihydropyridine Derivatives

Auria-Luna, F. ; Marqués-López, E. (Universidad de Zaragoza) ; Perez Herrera, R. (Universidad de Zaragoza)

Resumen: 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 ß-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.

Idioma: Inglés

DOI: 10.3390/molecules23102692

Año: 2018

Publicado en: Molecules 23, 10 (2018), 2692
ISSN: 1420-3049

Factor impacto JCR: 3.06 (2018)

Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 67 / 172 = 0.39 (2018) - Q2 - T2
Categ. JCR: BIOCHEMISTRY & MOLECULAR BIOLOGY rank: 133 / 294 = 0.452 (2018) - Q2 - T2

Factor impacto SCIMAGO: 0.757 - Analytical Chemistry (Q1) - Chemistry (miscellaneous) (Q1) - Drug Discovery (Q1) - Physical and Theoretical Chemistry (Q1) - Molecular Medicine (Q1) - Organic Chemistry (Q1) - Pharmaceutical Science (Q1) - Medicine (miscellaneous) (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E07-17R
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-88091-P
Financiación: info:eu-repo/grantAgreement/ES/UZ/JIUZ-2017-CIE-05

Tipo y forma: Article (Published version)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)