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

Autor:	Rengarajan Balamurugan, Ganesh Kumar Thota, Raveendra Babu Kothapalli
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Reaction mechanism Intramolecular reaction Bicyclic molecule Organic Chemistry Diol Acetal Alkyne Epoxide Homogeneous catalysis Combinatorial chemistry chemistry.chemical_compound chemistry Organic chemistry Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2011:1557-1569
ISSN:	1434-193X
DOI:	10.1002/ejoc.201001214
Popis:	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.
Databáze:	OpenAIRE
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