Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Synthesis of α-Acyloxyketone Derivatives via the Platinum-Catalyzed Migration of Propargylic Esters
Chihiro TsukanoSho YamamotoYoshiji Takemoto
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2015 Volume 63 Issue 9 Pages 710-719

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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 H218O.

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© 2015 The Pharmaceutical Society of Japan
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