Absolute configuration assignment of 3-indolylacetate esters
Meléndez Rodríguez, Myriam
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.
Related articles
Transesterifications mediated by t-BuNH2
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Mechanisticstudies of the photochemicalrearrangement of 1-oxolongipin-2-ene derivatives
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
First Total Synthesis of ()-Flustraminol B
Photochemical rearrangements of highly functionalized longipinene derivatives
Synthesis of Indolylindolines Mediated by tert-BuNH2
Cleavage of alkoxycarbonylprotectinggroups from carbamates by t-BuNH2