Absolute configuration assignment of 3-indolylacetate esters
Cruz Borbolla, Julian
2012
Vazquez-Arredondo, RM; Suarez-Castillo, OR ; Melendez-Rodriguez, M; Sanchez-Zavala, M; Cano-Escudero, IC ; Bautista-Hernandez, CI ; Cruz-Borbolla, J ; Morales-Rios, MS; Joseph-Nathan, P; Absolute configuration assignment of 3-indolylacetate esters TETRAHEDRON-ASYMMETRY. Año 2012, Volume: 23 Issue: 17 Pages: 1279-1293 DOI: 10.1016/j.tetasy.2012.08.005 ISSN: 0957-4166
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.
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