887922-07-8

Upstream product

• 92850-41-4 8-hydroxy-2-phenyl-5,6,7,8-tetrahydroquinoline 
• 98-88-4 benzoyl chloride 
• 887922-04-5 (8R)-2-phenyl-8-benzoyloxy-5,6,7,8-tetrahydroquinoline 
• 78590-01-9 8-oxo-2-phenyl-5,6,7,8-tetrahydroquinoline 
• 108-94-1 cyclohexanone 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 24740-01-0 2-(2-benzoylethyl)cyclohexanone 
• 879-72-1 3-(dimethylamino)propiophenone hydrochloride 
• 1570-04-3 2-phenyl-5,6,7,8-tetrahydroquinoline 
• 92850-39-0 2-phenyl-5,6,7,8-tetrahydroquinoline N-oxide 
• 98-86-2 acetophenone 

Downstream Products

• 912277-36-2 (R)-2-phenyl-5,6,7,8-tetrahydroquinolin-8-yl dicyclohexylphosphinite 
• 1431617-63-8 C₄₃H₄₀N₃O₃P 

Relevant academic research and scientific papers

Optimized Scalable Synthesis of Chiral Iridium Pyridyl-Phosphinite (Pyridophos) Catalysts

Iridium catalysts with chiral P,N ligands have greatly enhanced the scope of asymmetric olefin hydrogenation because they do not require a coordinating group near the C=C bond like Rh and Ru catalysts. Pyridophos ligands, possessing a conformationally restricted annulated pyridine framework linked to a phosphinite group, proved to be particularly effective, inducing high enantioselectivities in the hydrogenation of a remarkably broad range of substrates. Here we report the development of an efficient scalable synthesis for the two most versatile Ir-pyridophos catalysts, derived from 2-phenyl-8-hydroxy-5,6,7,8-tetrahydroquinoline or the analogue with a five-membered carbocyclic ring, respectively, by modification and optimization of the original synthetic route. The optimized route renders both catalysts readily accessible in multi-gram quantities in analytically pure form in overall yields of 26–37 %, starting from acetophenone and cyclopentanone or cyclohexanone, respectively. A major advantage of the new synthesis is the efficient and practical kinetic resolution of the late-stage pyridyl alcohol intermediates with commercial immobilized Candida antarctica lipase B, giving access to both enantiomers of these catalysts as essentially enantiopure compounds. The catalysts are obtained as crystalline solids, which are air-stable and can be stored for years at ?20 °C without notable decomposition.

Rhodium Catalyzed Asymmetric Hydrogenation of 2-Pyridine Ketones

Catalyzed by [Rh(COD)Binapine]BF4, the asymmetric hydrogenation of 2-pyridine ketones has been achieved with excellent enantioselectivities (enantiomeric excesses up to 99%) under mild conditions. This method is suitable for various kinds of 2-pyridine ketones and their derivatives. A number of enantiomerically pure chiral 2-pyridine-aryl/alkyl alcohols were prepared through hydrogenation, which can be used directly in organic synthesis.

Iron(ii)-bis(isonitrile) complexes: Novel catalysts in asymmetric transfer hydrogenations of aromatic and heteroaromatic ketones

Chiral iron(ii)-bis(isonitrile) complexes catalyse the transfer hydrogenation of aromatic ketones with enantioselectivities up to 91% ee, most likely via hydride transfer through imine intermediates, generated by in situ reduction of the isonitrile ligands, whereas iron acts as a Lewis acid to activate the ketone.

Design and synthesis of new chiral pyridine-phosphite ligands for the copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones

A series of new chiral pyridine-phosphite ligands have been prepared from (R)-pyridyl alcohols and BINOL-derived chlorophosphite, and successfully employed in the copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones. Using the simple and inexpensive CuBr2 as a precursor, the enantioselective additions to various substituted acyclic enones afforded products in high yields and good enantioselectivities (up to 92% ee).

Kinetic resolution of pyridyl alcohols by Cu(II)(borabox)-catalyzed acylation

Kinetic resolution of pyridyl alcohols has been achieved using copper(II)(borabox)-catalyzed benzoylation. Selectivity factors (k rel) of up to 125 have been observed and application to the synthesis of chiral pyridyl phosphine ligands is descr

Iridium catalysts with bicyclic pyridine-phosphinite ligands: Asymmetric hydrogenation of olefins and furan derivatives

(Chemical Equation Presented) Superior bicyclics: Iridium catalysts as 1 derived from pyridine-phosphinite ligands considerably extend the scope of asymmetric hydrogenation. In addition to various unfunctionalized and functionalized olefins, furans, and benzofurans, for which no catalysts were known before, are also hydrogenated with high enantioselectivity (see scheme).

Kinetic resolution of diols and pyridyl alcohols by cu(II)(borabox)- catalyzed acylation

Boron-bridged bisoxazoline (borabox) ligands have been used in the copper(II)-catalyzed benzoylation of pyridyl alcohols and 1,2-diols. Efficient kinetic resolution of 1,2-diols was achieved using both borabox and bisoxazoline (box) ligands. Borabox ligands induced high selectivities in the benzoylation of suitable pyridyl alcohols, where they outperformed bisoxazolines. In addition, highly enantioselective Cu(II)(borabox)-catalyzed benzoylation has been used for the synthesis of both enantiomers of a pyridyl alcohol.