Efficient Synthesis of γ-Keto Esters through Neighboring Carbonyl Group-Assisted Regioselective Hydration of 3-Alkynoates
Weibo Wang, Bo Xu and Gerald B. Hammond*
*Department of Chemistry, University of Louisville,
Louisville, Kentucky 40292, Email: gb.hammond
louisville.edu
W. Wang, B. Xu, G. B. Hammond, J. Org. Chem., 2009, 74, 1640-1643.
DOI: 10.1021/jo802450n
Abstract
A mild, atom-economical, Au(III)-catalyzed hydration of 3-alkynoates allows a practical one-step synthesis of a wide range of γ-keto esters in good yields, through a carbonyl group participation enabled by a favored 5-endo-dig cyclization.
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proposed mechanism
Key Words
ID: J42-Y2009-0560
