Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolinesviaSNAr
Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolinesviathe nucleophilic aromatic substitution (SNAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These reactions displayed a spectrum of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characters depending upon the stereochemical stability of the starting material. Low barrier substrates proceededviaDKR while higher barrier substrates proceededviaKR. On the other hand, substrates with intermediate stabilities displayed hallmarks of both DKR and KR. Finally, we also show that we can functionalize the atropisomerically enriched quinolines into pharmaceutically privileged scaffolds with minimal observed racemization.
Cardenas, Mariel M.,Saputra, Mirza A.,Gordon, Deane A.,Sanchez, Andrea N.,Yamamoto, Nobuyuki,Gustafson, Jeffrey L.
supporting information
p. 10087 - 10090
(2021/10/06)
Studies of one-pot double couplings on dibromoquinolines
In a series of studies, the regioselectivity of Suzuki couplings of dibromoquinolines has been investigated. In general, it is much harder to achieve high levels of regioselectivity in these systems compared to many of the other dibromoheteroaromatics that have been studied. Useful levels of selectivity could be achieved for both a 5,7-dibromoquinoline as well as 3,4-dibromoquinoline. Double Suzuki couplings could also be achieved on these two compounds.
Piala, Alexander,Mayi, Diyar,Handy, Scott T.
experimental part
p. 4147 - 4154
(2011/07/08)
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