Gold-Catalyzed Regioselective Hydration of Propargyl Acetates Assisted by a Neighboring Carbonyl Group: Access to α-Acyloxy Methyl Ketones and Synthesis of (±)-Actinopolymorphol B
Nayan Ghosh, Sanatan Nayak and Akhila K. Sahoo*
*School of Chemistry, University of Hyderabad, Hyderabad 500046, India, Email: aksscuohyd.ernet.in
N. Ghosh, S. Nayak, A. K. Sahoo, J. Org. Chem., 2011, 76, 500-511.
DOI: 10.1021/jo101995g (free Supporting Information)
A catalyst comprising of Ph3PAuCl and AgSbF6 efficiently hydrolyzes terminal alkyne groups of propargyl acetates in the absence of acid promoters at ambient temperature within a short time. Effective regioselective hydration is facilitated by the neighboring carbonyl group. Synthesis of actinopolymorphol B is achieved involving hydration of the propargyl acetate as the key step.
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