Synthesis of Chiral 1,3-Dienes through Ring-Closing Metathesis of Enantioenriched Enynes: Potential Precursors of Morphane Analogs
Título del documento: Synthesis of Chiral 1,3-Dienes through Ring-Closing Metathesis of Enantioenriched Enynes: Potential Precursors of Morphane Analogs
Revue: Anais da Academia Brasileira de Ciencias
Base de datos: PERIÓDICA
Número de sistema: 000419767
ISSN: 0001-3765
Autores: 1
1
1
1
Instituciones: 1Universidad de Alicante, Facultad de Ciencias, Alicante. España
Año:
Periodo: May
Volumen: 90
Número: 1
Paginación: 1059-1072
País: Brasil
Idioma: Inglés
Tipo de documento: Artículo
Enfoque: Experimental, aplicado
Resumen en inglés A simple methodology for the synthesis of enynes by indium mediated diastereoselective allylation of aromatic N-tert-butanesulfinylimines bearing alkenyl groups at ortho-position with allyl bromide has been developed. The addition of the allyl indium intermediate to the chiral imine took place with excellent diastereoselectivity. Ruthenium-catalyzed ring-closing metathesis of the resulting enynes provided the expected cyclic 1,3-dienes in good to moderate yields. These chiral dienes are potential precursors of biologically and pharmacologically active morphane derivatives
Disciplinas: Medicina,
Química
Palabras clave: Química farmacéutica,
Compuestos quirales,
Síntesis química,
Eninas,
Alilación,
Metátesis,
Alcaloides
Keyword: Medicinal chemistry,
Chiral compounds,
Chemical synthesis,
Enynes,
Allylation,
Metathesis,
Alkaloids
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