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

Alexander F G Maier; Sebastian Tussing; Hui Zhu; Garrit Wicker; Pavleta Tzvetkova; Ulrich Flörke; Constantin G Daniliuc; Stefan Grimme; Jan Paradies

doi:10.1002/chem.201804777

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

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

Authors

Alexander F G Maier¹, Sebastian Tussing¹, Hui Zhu², Garrit Wicker¹, Pavleta Tzvetkova³, Ulrich Flörke¹, Constantin G Daniliuc⁴, Stefan Grimme², Jan Paradies¹

Affiliations

¹ Department of Chemistry, University of Paderborn, Warburger Strasse 100, 33098, Paderborn, Germany.
² Mulliken Center for Theoretical Chemistry, University of Bonn, Beringstr. 4, 53115, Bonn, Germany.
³ Institute of Organic Chemistry and Institute for Biological Interfaces-4, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
⁴ Institute of Organic Chemistry, University of Münster, Corrensstrasse 40, 48149, Münster, Germany.

PMID: 30230618
DOI: 10.1002/chem.201804777

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.

Abstract

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