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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)


Abstract

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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Key Words

α-hydroxy ketones, hydrolysis of alkynes


ID: J42-Y2011-0090