State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China, Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University , 3663 North Zhongshan Lu, Shanghai 200062, P. R. China, and Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University , Hangzhou 310027, Zhejiang, P. R. China.
Org Lett. 2012 Jul 20;14(14):3616-9. doi: 10.1021/ol301408g. Epub 2012 Jul 3.
Gold-catalyzed cyclization reactions of indoles with an electron-deficient allene at the 3-position led to formation of dihydrocyclopenta[b]indole derivatives in moderate to excellent yields via C2-H bond functionalization of the indole unit. The presence of the electron-withdrawing alkoxycarbonyl, dialkoxyphosphono, or phenyl is crutial for this transformation. The potential synthetic dihydrocyclopenta[b]indole with the electron-withdrawing group has been demonstrated by applying a [3 + 2] cycloaddition reaction to construct the tretracycloskeleton.
金催化的吲哚与 3-位缺电子烯丙基的环化反应，通过吲哚单元的 C2-H 键功能化，以中等至优异的收率得到二氢环戊[b]吲哚衍生物。吸电子烷氧基羰基、二烷氧基膦酰基或苯基的存在对这种转化至关重要。通过应用[3+2]环加成反应构建三环骨架，展示了具有吸电子基团的潜在合成二氢环戊[b]吲哚。
