Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade

Thomas Sephton; Jonathan m. Large; Sam Butterworth; Michael f. Greaney

doi:10.1021/acs.orglett.3c02559

Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade

Thomas Sephton, Jonathan m. Large, Sam Butterworth, Michael f. Greaney

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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.

Original language	English
Journal	Organic Letters
Early online date	5 Sept 2023
DOIs	https://doi.org/10.1021/acs.orglett.3c02559
Publication status	E-pub ahead of print - 5 Sept 2023

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10.1021/acs.orglett.3c02559Licence: CC BY

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title = "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.",

author = "Thomas Sephton and Large, {Jonathan m.} and Sam Butterworth and Greaney, {Michael f.}",

year = "2023",

month = sep,

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doi = "10.1021/acs.orglett.3c02559",

language = "English",

journal = "Organic Letters",

issn = "1523-7052",

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T1 - Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade

AU - Sephton, Thomas

AU - Large, Jonathan m.

AU - Butterworth, Sam

AU - Greaney, Michael f.

PY - 2023/9/5

Y1 - 2023/9/5

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.3c02559

DO - 10.1021/acs.orglett.3c02559

M3 - Article

SN - 1523-7052

JO - Organic Letters

JF - Organic Letters

ER -

Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade

Abstract

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