A synthetic method to prepare 1-naphthyl ketones from gold(i)-catalysed oxidative cycloisomerisation of 1,6-diyne acetates is described. The proposed mechanism involves cyclopropenation–cycloreversion of the 1,6-diyne motif initiated by a 1,2-acyloxy migration. This is followed by nucleophilic attack of the ensuing gold carbenoid species by a molecule of water and autoxidation to give the aromatic product.
A synthetic method to prepare 1H-indenes and partially hydrogenated methanonaphtho[1,2-c]furan-1,3(4H)-diones from gold(i)-catalysed 1,4-enyne acetate cycloisomerisation and oxidation or Diels–Alder reaction with maleic anhydride is described. The proposed mechanism involves Rautenstrauch rearrangement of the 1,4-enyne motif to give an insitu formed 1,3-cyclopentadiene intermediate. This is followed by 6-endo-dig cyclisation of the cyclic adduct and oxidation to give the aromatic carbocycle or Diels–Alder reaction with maleic anhydride to afford the bridged furan product.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.