Abstract
The gold(I)-catalyzed intramolecular hydroamination of cyclohexa-1,3-dienes bearing an arylsulfonamide at the C-5 position proceeds in a 1,4-addition manner to afford hexahydroindole derivatives in a diastereoselective fashion and in good yields, whereas octahydrocyclohepta[b]pyrrole derivatives can be obtained from seven-membered ring substrates under the same reaction conditions. Coordination of the gold(I) species to the 1,3-diene at the double bond adjacent to the arylsulfonamide tether gave an η2-alkene gold complex. The anti-attack of the sulfonamide to the η2-alkene gold complex at the terminal position of the 1,3-diene resulted in the formation of the fused bicyclic ring with a newly formed Au-C bond at the allylic position. Allylic rearrangement of the η1-allylgold complex followed by protodemetalation provided the fused heterobicyclic skeletons and regenerated the catalyst.
Original language | English |
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Pages (from-to) | 4789-4794 |
Number of pages | 6 |
Journal | Tetrahedron |
Volume | 65 |
Issue number | 25 |
DOIs | |
Publication status | Published - 2009 Jun 20 |
Keywords
- Cycloheptadiene
- Cyclohexadiene
- Gold-catalyzed
- Hexahydroindoles
- Hydroamination
- Intramolecular
- Octahydrocyclohepta[b]pyrroles
- Sulfonamide
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry