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.
Related articles
Role of lipid peroxidation in biliary obstruction in the rat.
Transesterifications mediated by t-BuNH2
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Trapping enols of esters and lactones with diazomethane
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase
One-potsynthesis of conformationallyrestrictedspirooxindoles