Abstract
| - Reaction of benzyl (2,2-diphenyl-4,5-hexadienyl)carbamate (4) with a catalytic 1:1 mixture ofAu[P(t-Bu)2(o-biphenyl)]Cl (2) and AgOTf (5 mol %) in dioxane at 25 °C for 45 min led to isolation of benzyl4,4-diphenyl-2-vinylpyrrolidine-1-carboxylate (5) in 95% yield. The Au(I)-catalyzed intramolecular hydroamination of N-allenyl carbamates tolerated substitution at the alkyl and allenyl carbon atoms and was effectivefor the formation of piperidine derivatives. γ-Hydroxy and δ-hydroxy allenes also underwent Au-catalyzedintramolecular hydroalkoxylation within minutes at room temperature to form the corresponding oxygenheterocycles in good yield with high exo-selectivity. 2-Allenyl indoles underwent Au-catalyzed intramolecularhydroarylation within minutes at room temperature to form 4-vinyl tetrahydrocarbazoles in good yield. Au-catalyzed cyclization of N-allenyl carbamates, allenyl alcohols, and 2-allenyl indoles that possessed anaxially chiral allenyl moiety occurred with transfer of chirality from the allenyl moiety to the newly formedstereogenic tetrahedral carbon atom.
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