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.
Artículos relacionados
The absoluteconfiguration of cuauhtemone and related compounds
First Total Synthesis of ()-Flustraminol B
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea
One-potsynthesis of conformationallyrestrictedspirooxindoles
Role of lipid peroxidation in biliary obstruction in the rat
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor