Producción Científica Profesorado

Absolute configuration assignment of 3-indolylacetate esters

Suárez Castillo, Oscar Rodolfo


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.


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.

Producto de Investigación

Artículos relacionados

Synthesis of ?4:?2-Exocyclic-Diene Iridium(I) Complexes Derived from 1,3-Oxazolidin-2-ones and Their...

One-potsynthesis of conformationallyrestrictedspirooxindoles

Synthesis of Indolylindolines Mediated by tert-BuNH2

Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters

Role of lipid peroxidation in biliary obstruction in the rat

Reactivity of TpMe2Ir(C2H4)(DMAD) with carboxylic acids. A DFT study on geometrical isomers and stru...

Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2

13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters

Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine

Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles