Producción Científica Profesorado

Absolute configuration assignment of 3-indolylacetate esters



Suárez Castillo, Oscar Rodolfo

2012

Rosa M. Vázquez-Arredondo, Oscar R. Suárez-Castillo, Myriam Meléndez-Rodríguez, Maricruz Sánchez-Zavala, Indira C. Cano-Escudero, Claudia I. Bautista-Hernández, Julián Cruz-Borbolla, Martha S. Morales-Ríos, Pedro Joseph-Nathan. Absolute con?guration assignment of 3-indolylacetate esters. TETRAHEDRON-ASYMMETRY. Año: 2012, Volume: 23 Issue: 17 Pages: 1279-1293 DOI: 10.1016/j.tetasy.2012.08.005


Abstract


Herein we describe a straightforward method for the determination of the absolute con?guration of 3-indolyl(bromo)acetate 7, 3-indolyl(alkoxy)acetates 8a?f and 3-indolyl(amino)acetate 8g, based on 1HNMR spectral analysis. The conformational preferences for two diastereomeric esters were calculatedby DFT, which matched very well with the experimental results. X-ray diffraction analysis allowed usto validate the methodology, and independent absolute con?guration evidence was obtained by vibrational circular dichroism.



Producto de Investigación




Artículos relacionados

Cascade [1,3]-Sigmatropic Rearrangements of Ketene O,O-Acetals: Kinetic and DFT Level Mechanistic St...

Synthesis of Indolylindolines Mediated by tert-BuNH2

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

Firsttotalsyntheses of dihydroflustramine C and flustramine E, alkaloids from the marine bryozoan Fl...

Role of lipid peroxidation in biliary obstruction in the rat

Trapping enols of esters and lactones with diazomethane

Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Synthesis of Acetamido(indol-3-yl)propanol Derivatives

Conformationalstudies of N-carbomethoxy-2-alkoxyindolenines by dynamic NMR, crystallography, and mol...