Producción Científica Profesorado

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.



Producto de Investigación




Artículos relacionados

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

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

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

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives

Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

Trapping enols of esters and lactones with diazomethane

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

Synthesis of Indolylindolines Mediated by tert-BuNH2

Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling