Producción Científica Profesorado

One-potsynthesis of conformationallyrestrictedspirooxindoles



Suárez Castillo, Oscar Rodolfo

2007

One-pot synthesis of conformationally restricted spirooxindoles. Martha S. Morales-Ríos, Daphne E. González-Juárez, Ernesto Rivera-Becerril, Oscar R. Suárez-Castillo, Pedro Joseph-Nathan. DOI: http://dx.doi.org/10.1016/j.tet.2007.05.009


Abstract


Diastereomeric three-, five- and six-membered spirocycloalkyloxindoles were successfully synthesized in a rapid and convenient manner from readily accessible starting materials in moderate to high yields using 1-methyl-3-acetonitriloxindole after a one-pot base-mediated double-alkylation strategy. It was found that the diastereoselection is dependent on the reaction conditions and the spirocycloalkyl ring size, with the 3R?,8R? diastereomers being thermodynamically favored under the basic reaction conditions for three- and five-membered rings, and the 3R?,8S? diastereomer in the case of six-membered rings, as predicted by DFT calculations. The relative stereochemistry was supported by 2D NMR spectra and X-ray crystal structural analysis. The conformational rigidity of the spirocycloalkyloxindoles in solution was established based on NMR experimental and theoretical DFT approaches.



Producto de Investigación




Artículos relacionados

13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters

Trapping enols of esters and lactones with diazomethane

Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea

Role of lipid peroxidation in biliary obstruction in the rat

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

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

Reactivity of TpMe2Ir(C2H4)(DMAD) with carboxylic acids. A DFT study on geometrical isomers and stru...

Conformationalstudies of N-carbomethoxy-2-alkoxyindolenines by dynamic NMR, crystallography, and mol...

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

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates