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

Creative Commons You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.


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