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Gold‐Catalyzed Regioselective Tetradehydro‐Diels‐Alder Reaction of Yne‐Ynamides: Access to 2,3‐Dihydrobenzo[ f ]indoles
Author(s) -
Prabagar B.,
Dutta Shubham,
Gandon Vincent,
Sahoo Akhila K.
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900225
Subject(s) - regioselectivity , chemistry , alkyne , indole test , intramolecular force , catalysis , aryl , diels–alder reaction , density functional theory , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , computational chemistry , alkyl
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 (DFT) calculations. Substrates having an aryl group at the ynamide terminus are exclusively participating in this TDDA reaction under gold catalysis.