Research Grants Program Office (RGPO)
Dispersion-Controlled Regioselective Acid-Catalyzed Intramolecular Hydroindolation of cis-Methindolylstyrenes To Access Tetrahydrobenzo[ cd]indoles.
- Author(s): Cai, Xiao
- Tohti, Anargul
- Ramirez, Cristian
- Harb, Hassan
- Fettinger, James C
- Hratchian, Hrant P
- Stokes, Benjamin J
- et al.
Published Web Locationhttps://pubs.acs.org/doi/10.1021/acs.orglett.9b00043
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.
This item is under embargo until March 6, 2020.
You may have access to the publisher's version here:https://pubs.acs.org/doi/10.1021/acs.orglett.9b00043Notify me by email when this item becomes available