Synthesis of α-Acyloxyketone Derivatives via the Platinum-Catalyzed Migration of Propargylic Esters

Chemical & Pharmaceutical Bulletin
Chihiro TsukanoYoshiji Takemoto

Abstract

The synthesis of α-acyloxyketones via the migration of a propargylic ester followed by the intramolecular nucleophilic addition of the resulting allene was achieved using a cationic platinum catalyst. The optimized conditions for this transformation were determined to be 3 mol% of Pt(cod)Cl2, 3 mol% of AgNTf2, and 3 eq of water in toluene at 100 °C, and these conditions were successfully applied to the synthesis of a wide variety of α-aryl-α-acyloxyketones. The mechanism of this reaction was evaluated in detail based on the results of isotope labeling experiments using H2(18)O.

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Citations

Dec 5, 2017·Chemical & Pharmaceutical Bulletin·Chihiro TsukanoYoshiji Takemoto

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