The chemoselective C-and O-prenylation of cyclic 1,3-diketones was achieved by tuning the prenyl source and catalyst.In the presence of the solid acid Nafion,the coupling of 1,3-cyclohexanediones with isoprene gave C-...The chemoselective C-and O-prenylation of cyclic 1,3-diketones was achieved by tuning the prenyl source and catalyst.In the presence of the solid acid Nafion,the coupling of 1,3-cyclohexanediones with isoprene gave C-prenylated 5-chromenones.Alternatively,using prenol as the substrate with the Lewis acid Al Cl3 as the catalyst resulted in the exclusive O-prenylation of 1,3-cyclohexanediones.Notably,the resulting products could easily undergo aromatization to deliver prenylated resorcinols that are otherwise difficult to prepare.Our methodology is highly selective,atom-economical,operationally simple,easily scalable,and has potential applications throughout organic synthesis.展开更多
文摘The chemoselective C-and O-prenylation of cyclic 1,3-diketones was achieved by tuning the prenyl source and catalyst.In the presence of the solid acid Nafion,the coupling of 1,3-cyclohexanediones with isoprene gave C-prenylated 5-chromenones.Alternatively,using prenol as the substrate with the Lewis acid Al Cl3 as the catalyst resulted in the exclusive O-prenylation of 1,3-cyclohexanediones.Notably,the resulting products could easily undergo aromatization to deliver prenylated resorcinols that are otherwise difficult to prepare.Our methodology is highly selective,atom-economical,operationally simple,easily scalable,and has potential applications throughout organic synthesis.
