Absolute configuration assignment of 3-indolylacetate esters |
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| Authors: | 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 |
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| Affiliation: | 1. Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Mineral de la Reforma, Hidalgo 42184, Mexico;2. Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, México, DF 07000, Mexico |
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| 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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