Absolute configuration assignment of 3-indolylacetate esters.
Sánchez Zavala, Maricruz
2012
Vázquez-Arredondo, R. M., Suárez-Castillo, O. R., Meléndez-Rodríguez, M., Sánchez-Zavala, M., Cano-Escudero, I. C., Bautista-Hernández, C. I., Cruz-Borbolla, J., Morales-Ríos, M. S., & Joseph-Nathan, P. (2012). Absolute configuration assignment of 3-indolylacetate esters. Tetrahedron: Asymmetry 23, 1279-1293.
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
Artículos relacionados
Photochemical rearrangements of highly functionalized longipinene derivatives
Synthesis of Indolylindolines Mediated by tert-BuNH2
Cleavage of alkoxycarbonylprotectinggroups from carbamates by t-BuNH2
Transesterifications mediated by t-BuNH2
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
First Total Synthesis of ()-Flustraminol B
Mechanisticstudies of the photochemicalrearrangement of 1-oxolongipin-2-ene derivatives