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 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.

• Autores: David Rodriguez, Fredy A.; Maldonado Villamil, Mauricio; Guevara Pulido, James
• Tipo de recurso: Article of journal
• Fecha de publicación: 2020
• Institución: Universidad El Bosque
• Repositorio: Repositorio U. El Bosque
• Idioma: eng
• OAI Identifier: oai:repositorio.unbosque.edu.co:20.500.12495/3665
• Acceso en línea: http://hdl.handle.net/20.500.12495/3665; https://doi.org/10.1155/2020/9248793; https://repositorio.unbosque.edu.co
• Palabra clave: Reacciones químicas; Catálisis; Enzimas
• Rights: openAccess
• License: Attribution 4.0 International