Absolute configuration assignment of 3-indolylacetate esters
Suárez Castillo, Oscar Rodolfo
2012
Vázquez-Arredondo, R. M., Suárez-Castillo, O. R., Meléndez-Rodríguez, M., Sánchez-Zavala, M., Cano-Escudero, I. C., Bautista-Hernández, C. I., Cruz-Borbolla, J., Morales-Ríos, M. S., & Joseph-Nathan, P. (2012). Absolute configuration assignment of 3-indolylacetate esters. Tetrahedron: Asymmetry 23, 1279-1293.
Abstract
Herein we describe a straightforward method for the determination of the absolute configuration of 3-indolyl(bromo)acetate 7, 3-indolyl(alkoxy)acetates 8a?f and 3-indolyl(amino)acetate 8g, based on 1H NMR spectral analysis. The conformational preferences for two diastereomeric esters were calculated by DFT, which matched very well with the experimental results. X-ray diffraction analysis allowed us to validate the methodology, and independent absolute configuration evidence was obtained by vibrational circular dichroism.
Artículos relacionados
Role of lipid peroxidation in biliary obstruction in the rat
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii
Trapping enols of esters and lactones with diazomethane
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles
Synthesis of Indolylindolines Mediated by tert-BuNH2
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase
One-potsynthesis of conformationallyrestrictedspirooxindoles