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

AutorSonsona, Isaac G.; Marqués-López, Eugenia ; Herrera, Raquel P.
Palabras claveChromene
Benzopyran
2-amino-3-cyano-4H-chromene
Malononitrile
Enantioselective
Organocatalysis
Synthesis
Thiourea
Squaramide
Cinchona derivatives
Fecha de publicación2015
EditorMultidisciplinary Digital Publishing Institute
CitaciónSymmetry 7(3): 1519-1535 (2015)
ResumenThe 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: addition of naphthol compounds to substituted α,α-dicyanoolefins; addition of malononitrile to substituted o-vinylphenols; addition of malononitrile to N-protected o-iminophenols; Michael addition of nucleophiles to 2-iminochromene derivatives; and 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.
DescripciónThis article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license.
Versión del editorhttp://dx.doi.org/10.3390/sym7031519
URIhttp://hdl.handle.net/10261/123030
DOI10.3390/sym7031519
ISSN2073-8994
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