New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4'- (1',4'-dihydropyridine)] Derivatives

Auria-Luna, Fernando ; Marqués-López, Eugenia (Universidad de Zaragoza) ; Mohammadi, Somayeh ; Heiran, Roghayeh ; Herrera, P.R. (Universidad de Zaragoza)

Resumen: Herein, we report our preliminary results concerning the first promising asymmetric synthesis of highly functionalized 2-oxospiro-indole-3, 4'-(1', 4'-dihydropyridine)] via the reaction of an enamine with isatylidene malononitrile derivatives in the presence of a chiral base organocatalyst. The moderate, but promising, enantioselectivity observed (30%–58% ee (enantiomeric excess)) opens the door to a new area of research for the asymmetric construction of these appealing spirooxindole skeletons, whose enantioselective syntheses are still very limited.

Idioma: Inglés

DOI: 10.3390/molecules200915807

Año: 2015

Publicado en: Molecules 20, 9 (2015), 15807-15826
ISSN: 1420-3049

Factor impacto JCR: 2.465 (2015)

Categ. JCR: CHEMISTRY, ORGANIC rank: 24 / 59 = 0.407 (2015) - Q2 - T2

Factor impacto SCIMAGO: 0.57 - Analytical Chemistry (Q2) - Chemistry (miscellaneous) (Q2) - Drug Discovery (Q2) - Physical and Theoretical Chemistry (Q2) - Medicine (miscellaneous) (Q2) - Organic Chemistry (Q2) - Pharmaceutical Science (Q2) - Molecular Medicine (Q3)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E104
Financiación: info:eu-repo/grantAgreement/ES/MICINN/CTQ2013-44367-C2-1-P
Financiación: info:eu-repo/grantAgreement/ES/UZ/JIUZ-2014-CIE-07

Tipo y forma: Article (Published version)

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