Stereochemistry modulates the catalytic hydrogenolysis of nitrile-substituted cyclopropanes
2012; Elsevier BV; Volume: 68; Issue: 35 Linguagem: Inglês
10.1016/j.tet.2012.06.025
ISSN1464-5416
AutoresDaphne E. González‐Juárez, J. Benjamín García‐Vázquez, Violeta Zúñiga-García, Joel J. Trujillo‐Serrato, Oscar R. Suárez‐Castillo, Pedro Joseph‐Nathan, Martha S. Morales‐Ríos,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoAbstract 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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