Cu(I)-catalyzed intramolecular cyclization of alkynoic acids in aqueous media: a "click side reaction".
Alkynoic acids, in particular, 4-pentynoic acid derivatives, undergo intramolecular cyclizations to enol lactones under reaction conditions typically applied for the Cu(I)-catalyzed cycloaddition of terminal alkynes and azides (click chemistry). Starting from appropriate alkynoic acid derivatives, either enol lactones or 1,2,3-triazole click products can be obtained selectively by Cu(I) catalysis in aqueous media.
Mindt
Thomas L
TL
Department of Chemistry and Applied Biosciences, ETH Zurich, 8093 Zurich, Switzerland. thomas.mindt@pharma.ethz.ch
Schibli
Roger
R
D000480:Alkynes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D000480:Alkynes; D002264:Carboxylic Acids; D007783:Lactones; D014867:Water; D003300:Copper