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
Synthesis of Indolylindolines Mediated by tert-BuNH2
Transesterifications mediated by t-BuNH2
The absoluteconfiguration of cuauhtemone and related compounds
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Trapping enols of esters and lactones with diazomethane
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives