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.
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii
The absoluteconfiguration of cuauhtemone and related compounds
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
First Total Synthesis of ()-Flustraminol B
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2