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Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade.

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.

SUBMITTER: Sephton T

PROVIDER: S-EPMC10510726 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature

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Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade.

Sephton Thomas T Large Jonathan M JM Butterworth Sam S Greaney Michael F MF

Organic letters 20230905 36

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<sup>3</sup> electrophilic cent ...[more]

PMID: 37668613

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