Kinugasa reactions in water: from green chemistry to bioorthogonal labelling.
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.
Life Sciences Division, National Research Council of Canada, Ottawa, ON K1A 0R6, Canada.
Mariya
M
Chigrinova
Life Sciences Division, National Research Council of Canada, Ottawa, ON K1A 0R6, Canada.|Department of Chemistry, University of Ottawa, Ottawa, ON K1N 6N5, Canada.
Douglas A
DA
MacKenzie
Life Sciences Division, National Research Council of Canada, Ottawa, ON K1A 0R6, Canada.
Allison R
AR
Sherratt
Life Sciences Division, National Research Council of Canada, Ottawa, ON K1A 0R6, Canada.|Department of Chemistry, University of Ottawa, Ottawa, ON K1N 6N5, Canada.
Lawrence L W
LL
Cheung
John Paul
JP
Pezacki
Life Sciences Division, National Research Council of Canada, Ottawa, ON K1A 0R6, Canada. John.Pezacki@nrc-cnrc.gc.ca.|Department of Chemistry, University of Ottawa, Ottawa, ON K1N 6N5, Canada. John.Pezacki@nrc-cnrc.gc.ca.
Paul
P
Pezacki
D002384:Catalysis; D061565:Cycloaddition Reaction; D055772:Green Chemistry Technology; D009589:Nitrogen Oxides / Q000737:chemistry; D012997:Solvents / Q000737:chemistry*; D014867:Water / Q000737:chemistry*; D047090:beta-Lactams / Q000138:chemical synthesis*
D009589:Nitrogen Oxides; D012997:Solvents; D047090:beta-Lactams; C015388:nitrones; D014867:Water