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- Title
Induction of Axial Chirality in 8-Arylquinolines through Halogenation Reactions Using Bifunctional Organocatalysts.
- Authors
Miyaji, Ryota; Asano, Keisuke; Matsubara, Seijiro
- Abstract
The enantioselective syntheses of axially chiral heterobiaryls were accomplished through the aromatic electrophilic halogenation of 3-(quinolin-8-yl)phenols with bifunctional organocatalysts that control the molecular conformations during successive halogenations. Axially chiral quinoline derivatives, which have rarely been synthesized in an enantioselective catalytic manner, were afforded in moderate-to-good enantioselectivities through bromination, and an analogous protocol also enabled enantioselective iodination. In addition, this catalytic reaction, which allows enantioselective control through the use of mono- ortho-substituted substrates, allowed the asymmetric synthesis of 8-arylquinoline derivatives bearing two different halogen groups in high enantioselectivities.
- Subjects
CHIRALITY element; HALOGENATION; QUINOLINE derivatives; ENANTIOSELECTIVE catalysis; BROMINATION
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 42, p9996
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201701707