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Please use this identifier to cite or link to this item: http://hdl.handle.net/10651/10670

Title: Oxazolidinone cross-alkylation during Evans' asymmetric alkylation reaction
Author(s): Fresno López, Nieves
Pérez Fernández, Ruth
Goya Laza, Pilar
Jimeno Herránz, María Luisa
Alkorta Osoro, Ibón
Elguero Bertolini, José
Menéndez Taboada, Laura
García-Granda, Santiago
Keywords: Oxazolidinone; Asymmetric Alkylation; X-Ray Crystallography; Multinuclear Nmr; Dft Calculations
Issue date: 2011
Publisher version: http://dx.doi.org/10.1016/j.tet.2011.09.083
Citation: Tetrahedron, 67(47), P. 9104-9111 (2011); doi:10.1016/j.tet.2011.09.083
Abstract: Starting from Evans’ imidazolidin-2-one (1) two compounds were obtained by trans-N-acylation: the expected one 3 with S,R configuration and a second compound 5, that is, related to 3 by the loss of a CH(CH3)Cdouble bond; length as m-dashO fragment. The stereochemistry of 3 was established by NMR spectroscopy, mainly NOE experiments, as expected, the new center has an S configuration, the compound being thus S,R. The structure of compound 5 was determined by X-ray crystallography. A mechanism of formation of 5 was proposed.
URI: http://hdl.handle.net/10651/10670
ISSN: 0040-4020
Local identifier: 20111285
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