Oxazolidinone cross-alkylation during Evans’ asymmetric alkylation reaction |
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| Authors: | Nieves FresnoRuth Pé rez-Ferná ndez,Pilar GoyaMa Luisa Jimeno,Ibó n AlkortaJosé Elguero,Laura Mené ndez-Taboada,Santiago Garcí a-Granda |
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| Affiliation: | a Instituto de Química Médica, IQM-CSIC, Juan de la Cierva, 3, E-28006 Madrid, Spain
b Departamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, E-33006 Oviedo, Spain |
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| 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)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. |
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| Keywords: | Oxazolidinone Asymmetric alkylation X-ray crystallography Multinuclear NMR DFT calculations |
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