Producción Científica Profesorado

Absolute configuration assignment of 3-indolylacetate esters



Meléndez Rodríguez, Myriam

2012

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. Absolute con?guration assignment of 3-indolylacetate esters. TETRAHEDRON-ASYMMETRY. Año: 2012, Volume: 23 Issue: 17 Pages: 1279-1293 DOI: 10.1016/j.tetasy.2012.08.005


Abstract


Herein we describe a straightforward method for the determination of the absolute con?guration of 3-indolyl(bromo)acetate 7, 3-indolyl(alkoxy)acetates 8a?f and 3-indolyl(amino)acetate 8g, based on 1HNMR spectral analysis. The conformational preferences for two diastereomeric esters were calculatedby DFT, which matched very well with the experimental results. X-ray diffraction analysis allowed usto validate the methodology, and independent absolute con?guration evidence was obtained by vibrational circular dichroism.



Producto de Investigación




Artículos relacionados

Quirogane, Prenopsane, and Patzcuarane Skeletons Obtained by Photochemically Induced Molecular Rearr...

Mechanisticstudies of the photochemicalrearrangement of 1-oxolongipin-2-ene derivatives

DFT and NMR parameterized conformation of valeranone

Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of naturalp...

First Total Synthesis of ()-Flustraminol B

Transesterifications mediated by t-BuNH2

Conformationalstudies of N-carbomethoxy-2-alkoxyindolenines by dynamicNMR, crystallography, and mole...

Photochemical rearrangements of highly functionalized longipinene derivatives

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Cleavage of alkoxycarbonylprotectinggroups from carbamates by t-BuNH2