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.
The absoluteconfiguration of cuauhtemone and related compounds
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Trapping enols of esters and lactones with diazomethane
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters