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
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase
One-potsynthesis of conformationallyrestrictedspirooxindoles
13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea
The absoluteconfiguration of cuauhtemone and related compounds