2024-03-28T10:49:34Zhttps://uvadoc.uva.es/oai/requestoai:uvadoc.uva.es:10324/289512021-06-24T07:42:19Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
UVaDOC
author
Infante Blanco, Rebeca
author
Martín Álvarez, José Miguel
author
Andrés Juan, Celia
author
Nieto Román, Francisco Javier
2018-03-12T12:08:35Z
2018-07-07T23:40:44Z
2017
Organic Letters, 2017, 19 (7), pp 1516–1519
1523-7060
http://uvadoc.uva.es/handle/10324/28951
10.1021/acs.orglett.7b00252
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.
eng
Attribution-NonCommercial-NoDerivatives 4.0 International
Dimethylzinc-Mediated Addition of Phenylacetylene to α-Diketones Catalyzed by Chiral Perhydro-1,3-benzoxazines
info:eu-repo/semantics/article
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
URL
https://uvadoc.uva.es/bitstream/10324/28951/1/Dimethylzinc-Org-Lett-2017-postprint.pdf
File
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874ad87530cdf9ab5b3a797dbbddc6f3
150362
application/pdf
Dimethylzinc-Org-Lett-2017-postprint.pdf