Organocatalytic Cascade Reaction of Aliphatic Enals and Benzoylnitromethane: Synthesis of Enantioenriched Tetrasubstituted Cyclohexene Carbaldehyde
A new example of the reactivity of enals with benzoylnitromethane was studied in a Michael-Michael-Aldol-Dehydration quadruple organocascade reaction. The reaction unexpectedly yielded a tetrasubstituted cyclohexene carbaldehyde with excellent enantiomeric excess when crotonaldehyde was used as the...
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| Format: | Article |
| Language: | English |
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Wiley
2020-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2020/9248793 |
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| author | Fredy A. David Rodriguez Mauricio Maldonado Villamil James Guevara-Pulido |
| author_facet | Fredy A. David Rodriguez Mauricio Maldonado Villamil James Guevara-Pulido |
| author_sort | Fredy A. David Rodriguez |
| collection | DOAJ |
| description | A new example of the reactivity of enals with benzoylnitromethane was studied in a Michael-Michael-Aldol-Dehydration quadruple organocascade reaction. The reaction unexpectedly yielded a tetrasubstituted cyclohexene carbaldehyde with excellent enantiomeric excess when crotonaldehyde was used as the Michael-acceptor, whereas using (E)-Hex-2-enal as the Michael-acceptor formed a cyclic hemiacetal by steering the reaction into the intramolecular formation of the same intermediate via a Michael-Heterocyclization domino reaction. |
| format | Article |
| id | doaj-art-a18e4fccb00a447ab9a2229dd8dce543 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2020-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-a18e4fccb00a447ab9a2229dd8dce5432025-02-03T05:53:53ZengWileyJournal of Chemistry2090-90632090-90712020-01-01202010.1155/2020/92487939248793Organocatalytic Cascade Reaction of Aliphatic Enals and Benzoylnitromethane: Synthesis of Enantioenriched Tetrasubstituted Cyclohexene CarbaldehydeFredy A. David Rodriguez0Mauricio Maldonado Villamil1James Guevara-Pulido2Departamento de Química, Facultad de Ciencias, Universidad Nacional de Colombia-Sede Bogotá, Bogotá 11001, ColombiaDepartamento de Química, Facultad de Ciencias, Universidad Nacional de Colombia-Sede Bogotá, Bogotá 11001, ColombiaQuímica Farmacéutica, Universidad El Bosque, Bogotá 11001, ColombiaA new example of the reactivity of enals with benzoylnitromethane was studied in a Michael-Michael-Aldol-Dehydration quadruple organocascade reaction. The reaction unexpectedly yielded a tetrasubstituted cyclohexene carbaldehyde with excellent enantiomeric excess when crotonaldehyde was used as the Michael-acceptor, whereas using (E)-Hex-2-enal as the Michael-acceptor formed a cyclic hemiacetal by steering the reaction into the intramolecular formation of the same intermediate via a Michael-Heterocyclization domino reaction.http://dx.doi.org/10.1155/2020/9248793 |
| spellingShingle | Fredy A. David Rodriguez Mauricio Maldonado Villamil James Guevara-Pulido Organocatalytic Cascade Reaction of Aliphatic Enals and Benzoylnitromethane: Synthesis of Enantioenriched Tetrasubstituted Cyclohexene Carbaldehyde Journal of Chemistry |
| title | Organocatalytic Cascade Reaction of Aliphatic Enals and Benzoylnitromethane: Synthesis of Enantioenriched Tetrasubstituted Cyclohexene Carbaldehyde |
| title_full | Organocatalytic Cascade Reaction of Aliphatic Enals and Benzoylnitromethane: Synthesis of Enantioenriched Tetrasubstituted Cyclohexene Carbaldehyde |
| title_fullStr | Organocatalytic Cascade Reaction of Aliphatic Enals and Benzoylnitromethane: Synthesis of Enantioenriched Tetrasubstituted Cyclohexene Carbaldehyde |
| title_full_unstemmed | Organocatalytic Cascade Reaction of Aliphatic Enals and Benzoylnitromethane: Synthesis of Enantioenriched Tetrasubstituted Cyclohexene Carbaldehyde |
| title_short | Organocatalytic Cascade Reaction of Aliphatic Enals and Benzoylnitromethane: Synthesis of Enantioenriched Tetrasubstituted Cyclohexene Carbaldehyde |
| title_sort | organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehyde |
| url | http://dx.doi.org/10.1155/2020/9248793 |
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