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Enantioselective Synthesis of beta-Quaternary Carbon-Containing Chromanes and 3,4-Dihydropyrans via Cu-Catalyzed Intramolecular C-O Bond Formation

A copper-catalyzed efficient enantioselective construction of chiral quaternary carbon-containing chromanes and 3,4-dihydropyrans is reported. The desymmetric C-O coupling is enabled by a chiral dimethylcyclohexane-1,2-diamine ligand and provides the desired products in good yields with high enantioselectivities. This method presents a broad substrate scope and is applicable to diversely substituted aryl bromides and alkenyl bromides. The application is demonstrated by a gram-scale synthesis and derivatization of the products toward valuable building blocks.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Enantioselective reduction of alpha-substituted ketones mediated by the boronate ester TarB-NO2

A facile and mild reduction procedure is reported for the preparation of chiral secondary alcohols prepared from alpha-substituted ketones using sodium borohydride and the chiral boronate ester (l)-TarB-NO2. Direct reduction of substituted ketones bearing Lewis basic heteroatoms generally provided secondary alcohols of only modest enantiomeric excess likely due to either competition between the target carbonyl and the functionalized sidechains at the Lewis acidic boron atom in TarB-NO2 or the added steric bulk of the alpha-sidechain. As an alternative method, these substrates were synthesized using TarB-NO2 via a two-step procedure involving the reduction of an alpha-halo ketone to a chiral terminal epoxide, followed by regioselective/regiospecific epoxide opening by various nucleophiles. This procedure provides access to a variety of functionalized secondary alcohols including beta-hydroxy ethers, thioethers, nitriles, and amines with enantiomeric excesses of 94% and yields up to 98%.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Related Products of 68737-65-5, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.68737-65-5, Name is (1R,2R)-N,N’-Dimethyl-1,2-cyclohexanediamine, molecular formula is C8H18N2. In a Article£¬once mentioned of 68737-65-5

Enantioselective bromoaminocyclization of allyl N-tosylcarbamates catalyzed by a chiral phosphine-Sc(OTf)3 complex

An effective enantioselective bromoaminocyclization of allyl N-tosylcarbamates catalyzed by a chiral phosphine-Sc(OTf)3 complex is described. A wide variety of optically active oxazolidinone derivatives containing various functional groups can be obtained with high enantioselectivities.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, Application In Synthesis of (1R,2R)-N,N’-Dimethyl-1,2-cyclohexanediamine, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 68737-65-5, Name is (1R,2R)-N,N’-Dimethyl-1,2-cyclohexanediamine, molecular formula is C8H18N2. In a Patent, authors is £¬once mentioned of 68737-65-5

PERFLUORINATED 5,6-DIHYDRO-4H-1,3-OXAZIN-2-AMINE COMPOUNDS AS BETA-SECRETASE INHIBITORS AND METHODS OF USE

The present invention provides a new class of compounds useful for the modulation of beta-secretase enzyme (BACE) activity. The compounds have a general Formula I: wherein variables A4, A5, A6, A8, each of R1 and R2, R3 and R7 of Formula I, independently, are defined herein. The invention also provides pharmaceutical compositions comprising the compounds, and corresponding uses of the compounds and compositions for treatment of disorders and/or conditions related to A-beta plaque formation and deposition, resulting from the biological activity of BACE. Such BACE mediated disorders include, for example, Alzheimer’s Disease, cognitive deficits, cognitive impairments, schizophrenia and other central nervous system conditions. The invention further provides compounds of Formulas II and III, and sub-formula embodiments thereof, intermediates and processes and methods useful for the preparation of compounds of Formulas I-III.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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N,N’-dialkylated 1,2-diamine derivatives as new efficient ligands for RuCl2(PPh3)3 catalyzed asymmetric transfer hydrogenation of aromatic ketones

Chiral N,N’-dialkylated cyclohexanediamine derivatives ligands have been synthesized and used in an asymmetric transfer hydrogenation of aryl ketones. Optically active alcohols with up to 93% enantiomeric excess were obtained in high yield.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

68737-65-5, (1R,2R)-N,N’-Dimethyl-1,2-cyclohexanediamine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 56 Preparation of N-(4-methylphenyl)benzamide using 4-chlorotoluene and N,N’-dimethyl-trans-1,2-cyclohexanediamine at 110 C. An oven-dried resealable Schlenk tube was charged with CuI (20 mg, 0.105 mmol, 5.1 mol %), benzamide (250 mg, 2.06 mmol), K2CO3 (600 mg, 4.34 mmol), evacuated and backfilled with argon. N,N’-Dimethyl-trans-1,2-cyclohexanediamine (35 muL, 0.222 mmol, 11 mol %) and 4-chlorotoluene (1.0 mL, 8.44 mmol) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110 C. for 23 h. The resulting dark blue-green suspension was cooled to room temperature and filtered through a 0.5*1 cm pad of silica gel eluding with 10 mL of ethyl acetate. The light brown filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2*20 cm; hexane-ethyl acetate 2:1; 15 mL fractions). Fractions 4-10 were concentrated, the solid residue was suspended in 10 mL of hexane and filtered to provide 392 mg (90% yield) of the product as fine white needles.

68737-65-5, 68737-65-5 (1R,2R)-N,N’-Dimethyl-1,2-cyclohexanediamine 2733821, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; Buchwald, Stephen L.; Klapars, Artis; Antilla, Jon C.; Job, Gabriel E.; Wolter, Martina; Kwong, Fuk Y.; Nordmann, Gero; Hennessy, Edward J.; US2003/65187; (2003); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI