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
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Role of lipid peroxidation in biliary obstruction in the rat
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles
Transesterifications mediated by t-BuNH2
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase