2026-04-26T20:19:59Zhttps://uvadoc.uva.es/oai/request

oai:uvadoc.uva.es:10324/289512025-02-17T13:52:39Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543

Dimethylzinc-mediated addition of phenylacetylene to α-diketones catalyzed by chiral perhydro-1,3-benzoxazines Infante Blanco, Rebeca Martín Álvarez, José Miguel Andrés Juan, Celia Nieto Román, Francisco Javier Producción Científica 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. 2018-03-12T12:08:35Z 2018-07-07T23:40:44Z 2017 info:eu-repo/semantics/article Organic Letters, 2017, 19 (7), pp 1516–1519 1523-7060 http://uvadoc.uva.es/handle/10324/28951 10.1021/acs.orglett.7b00252 eng https://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b00252 info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by-nc-nd/4.0/ Attribution-NonCommercial-NoDerivatives 4.0 International American Chemical Society SI