Kinugasa reactions in water: From green chemistry to bioorthogonal labelling

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.3390/molecules20046959
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Name affiliation
  1. National Research Council of Canada. Medical Devices
FormatText, Article
Journal titleMolecules
ISSN1420-3049
Volume20
Issue4
Pages6959–6969
Abstract
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 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.
Publication date
PublisherMDPI AG
LanguageEnglish
Peer reviewedYes
NPARC number21275818
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