Efficient synthesis of gamma-keto esters through neighboring carbonyl group-assisted regioselective hydration of 3-alkynoates.
The Au(III)-catalyzed hydration of 3-alkynoates led to a practical one-step synthesis of gamma-keto esters in high yields, through a carbonyl group participation enabled by a favored 5-endodig cyclization. This mild-aqueous ethanol, room temperature, and atom-economical method has been used effectively with a wide range of substrates. Using the same conditions, a 2-alkynoate produced the corresponding beta-keto ester in high yield.
Wang
Weibo
W
Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, USA.
Xu
Bo
B
Hammond
Gerald B
GB
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D006046:Gold / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D014867:Water / Q000737:chemistry*
D000480:Alkynes; D004952:Esters; D007659:Ketones; D014867:Water; D006046:Gold