Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives
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 i...
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| Format: | Article |
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MDPI AG
2015-08-01
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| Series: | Symmetry |
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| Online Access: | http://www.mdpi.com/2073-8994/7/3/1519 |
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| author | Isaac G. Sonsona Eugenia Marqués-López Raquel P. Herrera |
| author_facet | Isaac G. Sonsona Eugenia Marqués-López Raquel P. Herrera |
| author_sort | Isaac G. Sonsona |
| collection | DOAJ |
| description | 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 α,α-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. |
| first_indexed | 2024-04-12T19:46:39Z |
| format | Article |
| id | doaj.art-900fded85d804ee6a220ab9a321ad614 |
| institution | Directory Open Access Journal |
| issn | 2073-8994 |
| language | English |
| last_indexed | 2024-04-12T19:46:39Z |
| publishDate | 2015-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Symmetry |
| spelling | doaj.art-900fded85d804ee6a220ab9a321ad6142022-12-22T03:18:56ZengMDPI AGSymmetry2073-89942015-08-01731519153510.3390/sym7031519sym7031519Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene DerivativesIsaac G. Sonsona0Eugenia Marqués-López1Raquel P. Herrera2Laboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/Pedro Cerbuna 12, Zaragoza E-50009, SpainLaboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/Pedro Cerbuna 12, Zaragoza E-50009, SpainLaboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/Pedro Cerbuna 12, Zaragoza E-50009, SpainThe 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 α,α-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.http://www.mdpi.com/2073-8994/7/3/1519chromenebenzopyran2-amino-3-cyano-4H-chromenemalononitrileenantioselectiveorganocatalysissynthesisthioureasquaramidecinchona derivatives |
| spellingShingle | Isaac G. Sonsona Eugenia Marqués-López Raquel P. Herrera Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives Symmetry chromene benzopyran 2-amino-3-cyano-4H-chromene malononitrile enantioselective organocatalysis synthesis thiourea squaramide cinchona derivatives |
| title | Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives |
| title_full | Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives |
| title_fullStr | Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives |
| title_full_unstemmed | Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives |
| title_short | Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives |
| title_sort | enantioselective organocatalyzed synthesis of 2 amino 3 cyano 4h chromene derivatives |
| topic | chromene benzopyran 2-amino-3-cyano-4H-chromene malononitrile enantioselective organocatalysis synthesis thiourea squaramide cinchona derivatives |
| url | http://www.mdpi.com/2073-8994/7/3/1519 |
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