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.
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea
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
Transesterifications mediated by t-BuNH2
13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine