Gold-catalysed activation of epoxides: Application in the synthesis of bicyclic ketals
Gold-catalysed generation of diol equivalents from epoxides and their intramolecular reaction with Ca≡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. Sequential activation of epoxide and alkyne moieties by a gold catalyst in acetone as solvent has been achieved. This strategyhas been employed to synthesise bicyclic ketals from epoxy alkynes. Copyright
VO(acac)2/TBHP catalyzed epoxidation of 2-(2-alkenyl)phenols. Highly regio- and diastereoselective oxidative cyclization to 2,3-dihydrobenzofuranols and 3-chromanols
The VO(acac)2/TBHP (1.5 mol%/1.3 equiv) system has been successfully used for the epoxidation of variously double bond substituted 2-(2-alkenyl)phenols under mild conditions. Moreover, a one-pot conversion to 2,3-dihydrobenzofuranols and 3-chro
Lattanzi, Alessandra,Scettri, Arrigo
p. 942 - 946
(2007/10/03)
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