Borane-Catalyzed Synthesis of Quinolines Bearing Tetrasubstituted Stereocenters by Hydride Abstraction-Induced Electrocyclization.
Alexander F G MaierSebastian TussingHui ZhuGarrit WickerPavleta TzvetkovaUlrich FlörkeConstantin G DaniliucStefan GrimmeJan ParadiesPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2018)
The borane-catalyzed synthesis of quinoline derivatives bearing tetrasubstituted stereocenters from vinyl anilines has been developed. Mechanistic studies and quantum-mechanical investigations support the hydride abstraction/electrocyclization/hydride addition mechanism. The products were obtained in up to 99 % yield with a diastereoselectivity of >99 % in favour for the 3a-5-cis isomer.