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Title: Dimethylzinc-Mediated Addition of Phenylacetylene to α-Diketones Catalyzed by Chiral Perhydro-1,3-benzoxazines
Authors: Infante, Rebeca
Martín Álvarez, José Miguel
Andrés Juan, Celia
Nieto Román, Francisco Javier
Issue Date: 2017
Publisher: American Chemical Society
Description: Producción Científica
Citation: 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
Peer Review: SI
DOI: 10.1021/acs.orglett.7b00252
Sponsor: Ministerio de Economía, Industria y Competitividad (Project CTQ2014-59870 P)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
Publisher Version:
Language: eng
Rights: info:eu-repo/semantics/openAccess
Appears in Collections:CINQUIMA - Artículos de revista
DEP67 - Artículos de revista

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