Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade
Thomas Sephton1, Jonathan M Large2, Sam Butterworth3
1School of Chemistry, University of Manchester, Manchester M13 9PL, U.K.
Abstract:
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 sp3 electrophilic centers in cascade processes.
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