Australian Journal of Chemistry ( IF 1.0 ) Pub Date : 2020-08-13 , DOI: 10.1071/ch20175 Xiaoyu Chen , Andrew Thomas Holm , Philip Wai Hong Chan
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 in situ 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.
中文翻译:
金催化的1,4-烯炔乙酸酯策略合成1H-茚并部分氢化的甲萘并[1,2-c]呋喃-1,3(4H)-二酮
一种由金(i)催化的1,4-乙炔乙酸酯环异构化和氧化或狄尔斯反应制备1 H-茚并部分氢化甲烷萘并[1,2- c ]呋喃-1,3(4 H)-二酮的合成方法描述了与马来酸酐的der木反应。所提出的机理涉及Rautenstrauch重排1,4-烯炔基序以得到原位形成的1,3-环戊二烯中间体。这之后是6-内-挖环状加合物和氧化环化,得到的芳族碳环或与马来酐,得到桥接的呋喃产物Diels-Alder反应。