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
Synthesis of Acetamido(indol-3-yl)propanol Derivatives
The absoluteconfiguration of cuauhtemone and related compounds
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Synthesis of Indolylindolines Mediated by tert-BuNH2
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase
One-potsynthesis of conformationallyrestrictedspirooxindoles