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.
Artículos relacionados
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Synthesis of Acetamido(indol-3-yl)propanol Derivatives
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
Transesterifications mediated by t-BuNH2
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Role of lipid peroxidation in biliary obstruction in the rat