Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade
Thomas Sephton, Jonathan M. Large, Sam Butterworth, Michael F. Greaney
Abstract
High Resolution Image Download MS PowerPoint Slide Arylsulfonamides have been found to react with cyclopropane diesters under simple base treatment to give α-arylated pyrrolidinones. This one-pot process comprises three steps: nucleophilic ring-opening of the cyclopropane, reaction of the resulting enolate in a Smiles-Truce aryl transfer, and lactam formation. The reaction represents a new, operationally simple approach to biologically active pyrrolidinones and expands Smiles-Truce arylation methods to encompass sp 3 electrophilic centers in cascade processes.
Topics & Concepts
CyclopropaneChemistrySmiles rearrangementPyrrolidinonesElectrophileCombinatorial chemistryNucleophileRing (chemistry)CascadeArylStereochemistryLactamOrganic chemistryCatalysisAlkylChromatographyCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions