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- Title
Gold(I)-Catalyzed Dearomative [2+2]-Cycloaddition of Indoles with Activated Allenes: A Combined Experimental-Computational Study.
- Authors
Ocello, Riccardo; De Nisi, Assunta; Jia, Minqiang; Yang, Qing ‐ Qing; Monari, Magda; Giacinto, Pietro; Bottoni, Andrea; Miscione, Gian Pietro; Bandini, Marco
- Abstract
The gold-catalyzed synthesis of methylidene 2,3-cyclobutane-indoles is documented through a combined experimental/computational investigation. Besides optimizing the racemic synthesis of the tricyclic indole compounds, the enantioselective variant is presented to its full extent. In particular, the scope of the reaction encompasses both aryloxyallenes and allenamides as electrophilic partners providing high yields and excellent stereochemical controls in the desired cycloadducts. The computational (DFT) investigation has fully elucidated the reaction mechanism providing clear evidence for a two-step reaction. Two parallel reaction pathways explain the regioisomeric products obtained under kinetic and thermodynamic conditions. In both cases, the dearomative CC bond-forming event turned out to be the rate-determining step.
- Subjects
METHYLIDENES; RING formation (Chemistry); INDOLE compounds; ELECTROPHILIC addition reactions; ALLENAMIDES
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 50, p18445
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201503598