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. 2018 Nov 2;24(61):16287-16291.
doi: 10.1002/chem.201804777. Epub 2018 Oct 5.

Borane-Catalyzed Synthesis of Quinolines Bearing Tetrasubstituted Stereocenters by Hydride Abstraction-Induced Electrocyclization

Alexander F G Maier  1 , Sebastian Tussing  1 , Hui Zhu  2 , Garrit Wicker  1 , Pavleta Tzvetkova  3 , Ulrich Flörke  1 , Constantin G Daniliuc  4 , Stefan Grimme  2 , Jan Paradies  1
Affiliations

Borane-Catalyzed Synthesis of Quinolines Bearing Tetrasubstituted Stereocenters by Hydride Abstraction-Induced Electrocyclization

Alexander F G Maier et al. Chemistry. .

Abstract

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.

Keywords: amines; borane catalysis; electrocyclization; hydride abstraction; tetrahydroquinoline.

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