Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis
Andrea Vopálenská, Vojtěch Dočekal, Simona Petrželová, Ivana Cı́sařová, Ján Veselý
Abstract
The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1-nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-to-good isolated yields (15-69%) with excellent stereochemical outcomes. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spirooxindole compounds.
Topics & Concepts
CyclopentanesBifunctionalOxindoleStereoselectivityChemistryCatalysisOrganocatalysisCombinatorial chemistryReaction conditionsOrganic chemistryEnantioselective synthesisAsymmetric Synthesis and CatalysisOxidative Organic Chemistry ReactionsSynthetic Organic Chemistry Methods