Event Information
Gold(I)-Catalyzed Hydroarylation of 2-Allenyl Indoles
- Abstract:
A 1:1 mixture of gold(I) complex Au[P(tBu)2o-biphenyl]Cl (1) and AgOTf in dioxane at room temperature for 30 minutes catalyzed the cyclization of 2-(5-cyclohexylidene-2,2-dicarbomethoxy-penta-4,5-dienyl)-1-methyl-1H-indole (2) to 2,2-dicarbomethoxy-9-Methyl-4-cyclohexylidenemethyl-2,3,4,9-tetrahydro-1H-carbazole (3) in 89 % isolated yield. This mixture also catalyzed the cyclizations of 1-methyl-2-(2,2-dicarbomethoxy-6-ethyl-4,5-heptadienyl)-1H-indole (4) to 2,2-dicarbomethoxy-9-methyl-4-(2-methyl-but-1-enyl)-2,3,4,9-tetrahydro-1H-carbazole in 45 minutes with 90% isolated yield(5). A 1:2 mixture of the gold complex Au2Cl2(3,5-tBu-4-MeO-BIPHEP) [BIPHEP = 2,2’-Bis(diphenylphosphino)-1,1’biphenyl] (6) and AgBF4 at 24 °C for 40 h catalyzed the asymmetric cyclization of 2 to 3 in 71% isolated yield with 69% ee and converted 4 to 5 in 89% isolated yield after 24 h with 83% ee (major, Z) and 49% ee (minor, E).
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