Palladium-catalyzed asymmetric hydrogenation of 3-phthalimido substituted quinolines.
نویسندگان
چکیده
Homogeneous Pd-catalyzed asymmetric hydrogenation of 3-phthalimido substituted quinolines was successfully developed, providing facile access to chiral substituted tetrahydroquinolines bearing two contiguous stereogenic centers with up to 90% ee.
منابع مشابه
Asymmetric Hydrogenation of Quinolines Catalyzed by Iridium Complexes of Monodentate BINOL-Derived Phosphoramidites
The monodentate BINOL-derived phosphoramidite PipPhos is used as ligand for the iridium-catalyzed asymmetric hydrogenation of 2and 2,6-substituted quinolines. If tri-ortho-tolylphosphine and/or chloride salts are used as additives enantioselectivities are strongly enhanced up to 89%. NMR indicates that no mixed complexes are formed upon addition of tri-ortho-tolylphosphine.
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A series of 2-substituted 3-(toluenesulfonamidoalkyl)indoles was synthesized by application of (EtO)(2)POH or iodine as the catalyst, and was hydrogenated using chiral Pd catalyst, giving the 2,3-disubstituted indolines with up to 97% ee.
متن کاملAsymmetric hydrogenation of quinolines catalyzed by iridium complexes of BINOL-derived diphosphonites.
A chiral diphosphonite, derived from BINOL and with an achiral diphenyl ether backbone, is an excellent ligand for the Ir-catalyzed asymmetric hydrogenation of quinolines; achiral P-ligands serving as possible additives (ee = 73-96%).
متن کاملAsymmetric Hydrogenation of Quinolines Catalyzed by Iridium with Chiral Ferrocenyloxazoline Derived N,P Ligands
Chiral ferrocenyloxazoline derived N,P ligands are used in the iridium-catalyzed asymmetric hydrogenation of quinolines, and up to 92% ee was obtained. The role of the planar chirality is also studied.
متن کاملCatalytic asymmetric hydrogenation of quinoline carbocycles: unusual chemoselectivity in the hydrogenation of quinolines.
The reduction of quinolines selectively took place on their carbocyclic rings to give 5,6,7,8-tetrahydroquinolines, when the hydrogenation was conducted in the presence of a Ru(η(3)-methallyl)2(cod)-PhTRAP catalyst. The chiral ruthenium catalyst converted 8-substituted quinolines into chiral 5,6,7,8-tetrahydroquinolines with up to 91 : 9 er.
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عنوان ژورنال:
- Chemical communications
دوره 50 67 شماره
صفحات -
تاریخ انتشار 2014