Asymmetric hydrogenation of quinolines with high substrate/catalyst ratio.
نویسندگان
چکیده
The chiral diphosphinite ligand derived from (R)-1,1'-spirobiindane-7,7'-diol has been found to be highly effective in the Ir-catalyzed asymmetric hydrogenation of quinolines with high substrate/catalyst ratio (up to 5000) and high enantioselectivity (up to 94% ee).
منابع مشابه
Asymmetric Hydrogenation of Quinolines and Isoquinolines Activated by ChloroformatesWe are grateful for the financial support from the National Science Foundation of China and Dalian Institute of Chemical Physics (K2004Eo3), Chinese Academy of Sciences
Despite significant progress in the area of asymmetric hydrogenation, the enantioselective hydrogenation of aromatic and heteroaromatic compounds still remains a major challenge. Only a few examples with moderate enantioselectivity, which rely on unique catalyst systems and suffer from a limited scope of suitable substrates, have been described so far. There are several reasons that might expla...
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The combination of the readily available chiral bisphosphine ligand Difluorphos with [Ir(COD)Cl](2) in THF resulted in a highly efficient catalyst system for asymmetric hydrogenation of quinolines at quite low catalyst loadings (0.05-0.002 mol%), affording the corresponding products with high enantioselectivities (up to 96%), excellent catalytic activities (TOF up to 3510 h(-1)) and productivit...
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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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0957-4166/$ see front matter 2010 Elsevier Ltd. A doi:10.1016/j.tetasy.2010.03.053 * Corresponding author. Tel.: +44 24 7652 3260; fa E-mail address: [email protected] (M. Wills) The first report of an asymmetric transfer hydrogenation, in formic acid/triethylamine, of quinolines is described. Using a Ru(II) catalyst containing a 4-carbon tether, products of up to 73% ee were formed, whilst...
متن کاملSynthesis of tunable bisphosphine ligands and their application in asymmetric hydrogenation of quinolines.
A series of tunable axial chiral bisphosphine ligands have been synthesized from (S)-MeO-Biphep. The Ir complex of the MeO-PEG-supported ligand (S)-4k has been successfully applied in asymmetric hydrogenation of quinolines with up to 92% ee. The catalyst system is air-stable and recyclable.
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عنوان ژورنال:
- Chemical communications
دوره 6 شماره
صفحات -
تاریخ انتشار 2007