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Oxazolidinone cross-alkylation during Evans' asymmetric alkylation reaction

AuthorsFresno, Nieves ; Pérez-Fernández, Ruth ; Goya, Pilar ; Jimeno, M. Luisa ; Alkorta, Ibon ; Elguero, José ; Menéndez-Taboada, Laura; García-Granda, Santiago
Asymmetric alkylation
X-ray crystallography
Multinuclear NMR
DFT calculations
Issue Date25-Nov-2011
CitationTetrahedron 67 (47) : 9104-9111 (2011)
AbstractStarting 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)C]O 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.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2011.09.083
Appears in Collections:(IQM) Artículos
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