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Publication Details:

Title: Gold Catalyzed Regioselective Tetradehydro Diels-Alder Reaction of Yne-Ynamides: Access to 2,3-Dihydrobenzo[f]indoles

Author(s)B. Prabagar,*† Shubham Dutta,† Vincent Gandon*‡¥ and Akhila K. Sahoo*† : Asian J. Org. Chem. 2019, 8, 1128 – 1132
Journal NameAsian Journal of Chemistry
journal image URLhttp://chemistry.uohyd.ac.in/~aks/wp-content/uploads/prabagarajoc.png

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Presented herein is a gold(I) catalyzed intramolecular tetradehydro-Diels-Alder (TDDA) reaction of alkyne-tethered-ynamides for the construction of structurally complex 2,3-dihydrobenzo[f]indole derivatives. The mechanism of the regioselective benzannulation reaction was rationalized by means of density functional theory calculations. Substrates having an aryl group at the ynamide terminus are exclusively participating in this TDDA reaction under gold catalysis.