Stereochemistry modulates the catalytic hydrogenolysis of nitrile-substituted cyclopropanes

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 spirocyclopropyloxin...

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Bibliographic Details
Published in:Tetrahedron 2012-09, Vol.68 (35), p.7187-7195
Main Authors: González-Juárez, Daphne E., García-Vázquez, J. Benjamín, Zúñiga-García, Violeta, Trujillo-Serrato, Joel J., Suárez-Castillo, Oscar R., Joseph-Nathan, Pedro, Morales-Ríos, Martha S.
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Chemoselectivity
Cyclopropane
DFT study
Exact sciences and technology
Hydrogenolysis
Organic chemistry
Preparations and properties
Regioselectivity
Stereochemistry
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.06.025