Premium
Borane‐Catalyzed Synthesis of Quinolines Bearing Tetrasubstituted Stereocenters by Hydride Abstraction‐Induced Electrocyclization
Author(s) -
Maier Alexander F. G.,
Tussing Sebastian,
Zhu Hui,
Wicker Garrit,
Tzvetkova Pavleta,
Flörke Ulrich,
Daniliuc Constantin G.,
Grimme Stefan,
Paradies Jan
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804777
Subject(s) - stereocenter , hydride , quinoline , borane , chemistry , catalysis , boranes , medicinal chemistry , combinatorial chemistry , organic chemistry , boron , enantioselective synthesis , hydrogen
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.