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.
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
The absoluteconfiguration of cuauhtemone and related compounds
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles
First Total Synthesis of ()-Flustraminol B
13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters
One-potsynthesis of conformationallyrestrictedspirooxindoles
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii