Producción Científica Profesorado

Stereochemistry modulates the catalytic hydrogenolysis of nitrile-substituted cyclopropanes



Suárez Castillo, Oscar Rodolfo

2012

Gonzalez-Juarez, D. E., García-Vazquez, J. B., Zuñiga-García, V., Trujillo-Serrato, J. J., Suárez-Castillo, O. R., Joseph-Nathan, P., & Morales-Ríos, M. S. (2012). Stereochemistry modulates the catalytic hydrogenolysis of nitrile-substituted cyclopropanes Tetrahedron 68, 7187-7195.


Abstract


The study of Raney-Ni catalyzed chemo- and regioselective hydrogenolysis of diastereomeric nitrile-substituted spirocyclopropyloxindoles is presented. The chemoselectivity outcome of the reaction is remarkably influenced by the relative stereochemistry of the nitrile-substituted spirocyclopropyloxindoles. Chemo- and high regioselective cyclopropane ring-opening occurs from the syn diastereomers to give the corresponding 3-propylacetamide derivatives. X-ray crystallographic studies together with DFT model chemistry calculations indicate that chemo- and regioselectivity are directly dependent on the bond length asymmetry of the cyclopropane ring



Producto de Investigación




Artículos relacionados

Synthesis of Acetamido(indol-3-yl)propanol Derivatives

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

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

The absoluteconfiguration of cuauhtemone and related compounds

Role of lipid peroxidation in biliary obstruction in the rat

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

Transesterifications mediated by t-BuNH2

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Trapping enols of esters and lactones with diazomethane

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