1326239-56-8Relevant academic research and scientific papers
Induction of Axial Chirality in 8-Arylquinolines through Halogenation Reactions Using Bifunctional Organocatalysts
Miyaji, Ryota,Asano, Keisuke,Matsubara, Seijiro
supporting information, p. 9996 - 10000 (2017/08/01)
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.
Asymmetric chroman synthesis via an intramolecular oxy-Michael addition by bifunctional organocatalysts
Miyaji, Ryota,Asano, Keisuke,Matsubara, Seijiro
supporting information, p. 119 - 122 (2014/01/06)
Cinchona-alkaloid-urea-based bifunctional organocatalysts facilitate the catalytic asymmetric synthesis of chroman derivatives via an intramolecular oxy-Michael addition reaction. Phenol derivatives bearing an easily available (E)-α,β-unsaturated ketone or a thioester moiety are useful substrates for the title transformation. This method represents a facile synthesis of various optically active 2-substituted chromans in high yield. The Royal Society of Chemistry.
Asymmetric indoline synthesis via intramolecular aza-Michael addition mediated by bifunctional organocatalysts
Miyaji, Ryota,Asano, Keisuke,Matsubara, Seijiro
, p. 3658 - 3661 (2013/08/23)
A novel method for the asymmetric synthesis of 2-substituted indolines, employing bifunctional amino(thio)urea catalysts, was developed. The reaction proceeded via an intramolecular aza-Michael addition mediated by activation through hydrogen bonding. The
Enantioselective organocatalytic aryloxylation of β-keto esters
Greenaway, Kevin,Dambruoso, Paolo,Ferrali, Alessandro,Hazelwood, Andrew J.,Sladojevich, Filippo,Dixon, Darren J.
supporting information; experimental part, p. 1880 - 1886 (2011/07/31)
An efficient enantioselective aryloxylation of cyclic β-keto esters with a selection of substituted o-quinones catalyzed by a bifunctional cinchona alkaloid derivative, giving entry to tricyclic dioxin adducts with high enantio- and diastereoselectivity, is described. Georg Thieme Verlag Stuttgart - New York.
