Suarez-Castillo, OR; Melendez-Rodriguez, M; Castelan-Duarte, LE; Zuniga-Estrada, EA; Cruz-Borbolla, J; Morales-Rios, MS ; Joseph-Nathan, P., Absolute configuration assignment of 3-oxindolylacetyl-4-phenyloxazolidinone derivativesTETRAHEDRON-ASYMMETRY. Año:2011 Volume: 22 Issue: 24 Pages: 2085-2098 DOI: 10.1016/j.tetasy.2011.11.018 .
The straightforward determination of the absolute configuration of 2-oxo-3-indolylacetic acid derivatives 5a?e, based on analysis of the 1H NMR spectra of their oxindolylacetyl-phenyloxazolidinones 6a?e, 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.