Absolute configuration assignment of 3-oxindolylacetyl-4-phenyloxazolidinone derivatives.
Suárez Castillo, Oscar Rodolfo
2011
Absolute configuration assignment of 3-oxindolylacetyl-4-phenyloxazolidinone derivatives. Oscar R. Suárez-Castilloa, , , Myriam Meléndez-Rodrígueza, Luis E. Castelán-Duartea, Erick A. Zúñiga-Estradaa, Julián Cruz-Borbollaa, Martha S. Morales-Ríosb, Pedro Joseph-Nathanb, Tetrahedron: Asymmetry 2011, 22, 2085209 http://dx.doi.org/10.1016/j.tetasy.2011.11.018,
Abstract
The straightforward determination of the absolute configuration of 2-oxo-3-indolylacetic acid derivatives 5ae, based on analysis of the 1H NMR spectra of their oxindolylacetyl-phenyloxazolidinones 6ae, is described. The conformational preferences for two diastereomeric amides were calculated by DFT, which matched well with the experimental results, while X-ray diffraction analysis allowed us to validate the methodology. Independent absolute configuration evidence was also obtained by vibrational circular dichroism.
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