Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 50, Pages 18445-18453Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201503598
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Funding
- University of Bologna
- MIUR Rome
- China Scholarship Council
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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 C-C bond forming event turned out to be the rate-determining step.
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