Dispersion-Controlled Regioselective Acid-Catalyzed Intramolecular Hydroindolation of cis -Methindolylstyrenes To Access Tetrahydrobenzo[ cd ]indoles
Year: 2019
Type: article
Abstract: Readily prepared cis-β-(α',α'-dimethyl)-4'-methindolylstyrenes undergo acid-catalyzed intramolecular hydroindolation to afford tetrahydrobenzo[ cd]indoles. Our experimental and computational investigations suggest that dispersive interactions between the indole and styrene preorganize substrates such that 6-membered ring formation is preferred, apparently via concerted protonation and C-C bond formation. When dispersion is attenuated (by a substituent or heteroatom), regioselectivity erodes and competing oligomerization predominates for cis substrates. Similarly, all trans-configured substrates that we evaluated failed to cyclize efficiently.
Source: Organic Letters
Authors: Xiao Cai, Anargul Tohti, Cristian Ramirez, Hassan Harb, James C. Fettinger, Hrant P. Hratchian, Benjamin J. Stokes
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $5,000
OpenAlex ID: W2917351441