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Efficient Synthesis of γ-Keto Esters through Neighboring Carbonyl Group-Assisted Regioselective Hydration of 3-Alkynoates

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journal contribution
posted on 20.02.2009, 00:00 by Weibo Wang, Bo Xu, Gerald B. Hammond
The Au(III)-catalyzed hydration of 3-alkynoates led to a practical one-step synthesis of γ-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 β-keto ester in high yield.