Enantioselective organocatalyzed synthesis of 2-amino-3-cyano-4H-chromene derivatives

Sonsona, I.G. ; Marqués-López, E. (Universidad de Zaragoza) ; Herrera, R.P. (Universidad de Zaragoza)

Resumen: The structural motif that results from the fusion of a benzene ring to a heterocyclic pyran ring, known as chromene, is broadly found in nature and it has been reported to be associated with a wide range of biological activity. Moreover, asymmetric organocatalysis is a discipline in expansion that is already recognized as a well-established tool for obtaining enantiomerically enriched compounds. This review covers the particular case of the asymmetric synthesis of 2-amino-3-cyano-4H-chromenes using organocatalysis. Herein, we show the most illustrative examples of the methods developed by diverse research groups, following a classification based on these five different approaches: (1) addition of naphthol compounds to substituted a, a-dicyanoolefins; (2) addition of malononitrile to substituted o-vinylphenols; (3) addition of malononitrile to N-protected o-iminophenols; (4) Michael addition of nucleophiles to 2-iminochromene derivatives; and (5) organocatalyzed formal 4+2] cycloaddition reaction. In most cases, chiral thioureas have been found to be effective catalysts to promote the synthetic processes, and generally a bifunctional mode of action has been envisioned for them. In addition, squaramides and cinchona derivatives have been occasionally used as suitable catalysts for the substrates activation.

Idioma: Inglés

DOI: 10.3390/sym7031519

Año: 2015

Publicado en: SYMMETRY-BASEL 7, 3 (2015), 1519-1535
ISSN: 2073-8994

Factor impacto JCR: 0.841 (2015)

Categ. JCR: MULTIDISCIPLINARY SCIENCES rank: 30 / 62 = 0.484 (2015) - Q2 - T2

Factor impacto SCIMAGO: 0.349 - Chemistry (miscellaneous) (Q2) - Computer Science (miscellaneous) (Q2) - Mathematics (miscellaneous) (Q3) - Physics and Astronomy (miscellaneous) (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)