2012
Gonzalez-Juarez, DE; Garcia-Vazquez, JB ; Zuniga-Garcia, V; Trujillo-Serrato, JJ; Suarez-Castillo, OR; Joseph-Nathan, P; Morales-Rios, MS., Stereochemistry modulates the catalytic hydrogenolysis of nitrile-substituted cyclopropanes. TETRAHEDRON , Año: 2012 Volume: 68 Issue: 35 Pages: 7187-7195 DOI: 10.1016/j.tet.2012.06.025 ISSN: 0040-4020
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.
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