Borane‐Catalyzed Synthesis of Quinolines Bearing Tetrasubstituted Stereocenters by Hydride Abstraction‐Induced Electrocyclization. Issue 61 (5th October 2018)

• Record Type: Journal Article
• Authors: Maier, Alexander F. G.; Tussing, Sebastian; Zhu, Hui; Wicker, Garrit; Tzvetkova, Pavleta; Flörke, Ulrich; Daniliuc, Constantin G.; Grimme, Stefan; Paradies, Jan
• Is Part Of: Chemistry. Volume 24:Issue 61(2018)
• Page Start: 16287
• Page End: 16291
• Publication Date: 2018-10-05
• Subjects: amines -- borane catalysis -- electrocyclization -- hydride abstraction -- tetrahydroquinoline; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201804777
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : It′s all in the abstract : The borane‐catalyzed synthesis of quinoline derivatives bearing tetrasubstituted stereocenters from vinyl anilines has been developed. Mechanistic and quantum‐mechanical investigations support the hydride abstraction/electrocyclization/hydride addition mechanism. The products were obtained in up to 97 % yield with a diastereoselectivity of >99 % for the 3a‐5‐ cis isomer.