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Gold-Catalysed Activation of Epoxides: Application in the Synthesis of Bicyclic Ketals

✍ Scribed by Rengarajan Balamurugan; Raveendra Babu Kothapalli; Ganesh Kumar Thota

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 866 KB
Volume: 2011
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.201001214

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✦ Synopsis

Abstract

Gold‐catalysed generation of diol equivalents from epoxides and their intramolecular reaction with C≡C bonds to generate bicyclic ketals is presented. This reaction essentially involves the formation of an acetonide, which subsequently cyclises on the alkyne intramolecularly under gold catalysis conditions. This method could be extended to make optically pure bicyclic ketals. Deuterium incorporation experiments were carried out to ascertain the mechanism of the reaction.

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