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.
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Synthesis of Indolylindolines Mediated by tert-BuNH2
One-potsynthesis of conformationallyrestrictedspirooxindoles
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters