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Gold-Catalyzed Cyclisation by 1,4-Dioxidation |
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| Authors: | Vanessa Claus Dr. Lise Molinari Simon Büllmann Jean Thusek Dr. Matthias Rudolph Dr. Frank Rominger Prof. Dr. A. Stephen K. Hashmi |
| Affiliation: | 1. Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany;2. Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany Crystallographic investigation |
| Abstract: | Amide-substituted diynes were cyclized in the presence of a cationic gold catalyst and an external nucleophile leading to 1-indenones and 1-iminoindenones. The electron-donating features of the nitrogen atom enable the formation of a reactive ketene iminium ion, which can be trapped by either diphenyl sulfoxide or anthranil as nucleophiles in a subsequent oxidation step, providing substituted inden-1-on-3-carboxamides. |
| Keywords: | cyclization diphenylsulfoxide diynes gold ynamides |