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Kinugasa reactions in water: from green chemistry to bioorthogonal labelling.

ABSTRACT: The Kinugasa reaction has become an efficient method for the direct synthesis of ?-lactams from substituted nitrones and copper(I) acetylides. In recent years, the reaction scope has been expanded to include the use of water as the solvent, and with micelle-promoted [3+2] cycloadditions followed by rearrangement furnishing high yields of ?-lactams. The high yields of stable products under aqueous conditions render the modified Kinugasa reaction amenable to metabolic labelling and bioorthogonal applications. Herein, the development of methods for use of the Kinugasa reaction in aqueous media is reviewed, with emphasis on its potential use as a bioorthogonal coupling strategy.

SUBMITTER: Chigrinova M

PROVIDER: S-EPMC6272444 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Kinugasa reactions in water: from green chemistry to bioorthogonal labelling.

Chigrinova Mariya M MacKenzie Douglas A DA Sherratt Allison R AR Cheung Lawrence L W LL Pezacki John Paul JP

Molecules (Basel, Switzerland) 20150416 4

The Kinugasa reaction has become an efficient method for the direct synthesis of β-lactams from substituted nitrones and copper(I) acetylides. In recent years, the reaction scope has been expanded to include the use of water as the solvent, and with micelle-promoted [3+2] cycloadditions followed by rearrangement furnishing high yields of β-lactams. The high yields of stable products under aqueous conditions render the modified Kinugasa reaction amenable to metabolic labelling and bioorthogonal a ...[more]

PMID: 25913933

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