Producción Científica Profesorado

Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives



Suárez Castillo, Oscar Rodolfo

2009

Suárez-Castillo Oscar R., Meléndez-Rodríguez Myriam, Castelán-Duarte Luis Enrique, Sánchez-Zavala Maricruz, Rivera-Becerril Ernesto, Morales-Ríos Martha S., Joseph-Nathan Pedro. Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives, Tetrahedron:Asymmetry 20, 23742389 (2009). ISSN 0957-4166. doi:10.1016/j.tetasy.2009.09.017


Abstract


We describe a reliable method for determining the absolute configuration of 2-(2-oxo-3-indolyl)acetamides based on analysis of the 1H NMR spectra of their phenylethylamide diastereomers. The conformational preferences for two diastereomeric amides were calculated by DFT, which matched well with the experimental results. X-ray diffraction analysis allowed us to validate the method.



Producto de Investigación




Artículos relacionados

Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

One-potsynthesis of conformationallyrestrictedspirooxindoles

Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

Trapping enols of esters and lactones with diazomethane

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling

Cascade [1,3]-Sigmatropic Rearrangements of Ketene O,O-Acetals: Kinetic and DFT Level Mechanistic St...

First Total Synthesis of ()-Flustraminol B

Transesterifications mediated by t-BuNH2