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

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

Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine

Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase

The absoluteconfiguration of cuauhtemone and related compounds

Role of lipid peroxidation in biliary obstruction in the rat

Transesterifications mediated by t-BuNH2

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

Synthesis of Indolylindolines Mediated by tert-BuNH2

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

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