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Título
Dimethylzinc-Mediated Addition of Phenylacetylene to α-Diketones Catalyzed by Chiral Perhydro-1,3-benzoxazines
Autor
Año del Documento
2017
Editorial
American Chemical Society
Descripción
Producción Científica
Documento Fuente
Organic Letters, 2017, 19 (7), pp 1516–1519
Abstract
An efficient enantioselective Me2Zn-mediated mono addition of phenylacetylene to α-diketones in the presence of a chiral perhydro-1,3-benzoxazine ligand is described. At temperatures higher than -20 ºC a kinetic resolution of the resulting α-hydroxy ketone occurs which greatly improves the enantioselectivity although with moderate chemical yield. The alkynylation of nonsymmetrical aromatic diketones with electronically different substituents on the aromatic rings proceed with high regioselectivity. This procedure allows the preparation of α-hydroxy-α-ynyl-ketones as highly enantioenriched materials.
ISSN
1523-7060
Revisión por pares
SI
Patrocinador
Ministerio de Economía, Industria y Competitividad (Project CTQ2014-59870 P)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
Version del Editor
Idioma
eng
Derechos
openAccess
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