- Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl-Ene Reaction
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An efficient desymmetrizing carbonyl-ene reaction of 1-substituted 4-methylenecyclohexanes with glyoxal derivatives was thus executed by a chiral N,N′-dioxide/NiII catalyst, providing facile access to cyclohexene derivatives bearing two remote 1,6-related stereocenters. This distal stereocontrol methodology originates from the efficient interaction between the catalyst with enophiles, discrimination of the two chair conformations of olefinic components, and the intrinsic six-membered transition-state structure of ene process.
- Luo, Weiwei,Lin, Lili,Zhang, Yu,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 3374 - 3377
(2017/07/15)
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- NOVEL GLP-1 RECEPTOR MODULATORS
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Compounds are provided that modulate the glucagon-like peptide 1 (GLP-1) receptor, as well as methods of their synthesis, and methods of their therapeutic and/or prophylactic use. Such compounds can act as modulators or potentiators of GLP-1 receptor on their own, or with incretin peptides such as GLP-1(7-36), GLP-1(9-36), and oxyntomodulin, or with peptide-based therapies, such as exenatide and liraglutide, and have the following general structure (where "?" represents either or both the R and S form of the compound): where A, B, C, R1, R2, R3, R4, R5, n, p and q are as defined herein.
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Paragraph 0393
(2016/02/09)
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- Highly Selective Hydrogenation of Aromatic Ketones and Phenols Enabled by Cyclic (Amino)(alkyl)carbene Rhodium Complexes
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Air-stable Rh complexes ligated by strongly σ-donating cyclic (amino)(alkyl)carbenes (CAACs) show unique catalytic activity for the selective hydrogenation of aromatic ketones and phenols by reducing the aryl groups. The use of CAAC ligands is essential for achieving high selectivity and conversion. This method is characterized by its good compatibility with unsaturated ketones, esters, carboxylic acids, amides, and amino acids and is scalable without detriment to its efficiency.
- Wei, Yu,Rao, Bin,Cong, Xuefeng,Zeng, Xiaoming
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supporting information
p. 9250 - 9253
(2015/08/11)
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- Synthesis and evaluations of GLP-1 secretion and anti-diabetic effect in KKAy mice of new tricyclic compounds
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Glucagon-like peptide-1 (GLP-1), which belongs to the family of incretins, plays important role for the regulation of plasma glucose. Accordingly, GLP-1-based therapies for type 2 diabetes have recognized as one of the most interesting target. In this study, we have found the new tricyclic compounds having strong GLP-1 secretion from human intestinal L cells, and anti-diabetic properties in spontaneously obese and diabetic KKAy mice. The most potent compound 5ka was obtained as the unexpected product, and we would like to report the details of the synthesis, structure elucidations, pharmacological activities on secretion of GLP-1, and anti-diabetic effects using diabetic KKAy mice.
- Minehira, Daisuke,Takeda, Daisuke,Miyawaki, Shota,Kato, Atsushi,Adachi, Isao,Miyazaki, Akira,Miyatake, Ryuta,Umezaki, Masahito,Miura, Kyoko,Kitahara, Yoshiro,Sugimoto, Kenji,Matsuya, Yuji,Toyooka, Naoki
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p. 372 - 404
(2015/03/04)
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- Rhodium-on-carbon catalyzed hydrogen scavenger- and oxidant-free dehydrogenation of alcohols in aqueous media
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The efficient and catalytic dehydrogenation of alcohols is a clean approach for preparing carbonyl compounds accompanied only by the generation of hydrogen gas. We have accomplished the heterogeneous rhodium-on-carbon catalyzed dehydrogenation of secondary, as well as primary, alcohols to the corresponding ketones and carboxylic acids in water under basic conditions. This journal is the Partner Organisations 2014.
- Sawama, Yoshinari,Morita, Kosuke,Yamada, Tsuyoshi,Nagata, Saori,Yabe, Yuki,Monguchi, Yasunari,Sajiki, Hironao
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supporting information
p. 3439 - 3443
(2014/07/08)
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- The catalytic asymmetric Fischer indolization
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The first catalytic asymmetric Fischer indolization is reported. In the presence of a 5 mol % loading of a novel spirocyclic chiral phosphoric acid, 4-substituted cyclohexanone-derived phenylhydrazones undergo a highly enantioselective indolization. Efficient catalyst turnover was achieved by the addition of a weakly acidic cation exchange resin, which removes the generated ammonia. The reaction can be conducted under mild conditions and gives various 3-substituted tetrahydrocarbazoles in generally high yields.
- Mueller, Steffen,Webber, Matthew J.,List, Benjamin
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supporting information; experimental part
p. 18534 - 18537
(2012/01/31)
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- Process for producing alicyclic monoketones and process for producing alicyclic diketones
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The process for producing alicyclic monoketones (hydroxyphenylcyclohexanone derivatives) according to the present invention comprises hydrogenating substituted bisphenols such as bisphenol A in a solvent in the presence of a palladium/alkali metal catalyst in which palladium and an alkali metal are both supported on a carrier to obtain alicyclic monoketones such as 2-(4-oxocyclohexyl)-2-(4-hydroxyphenyl)propane. The process for producing alicyclic diketones according to the present invention comprises hydrogenating substituted bisphenols such as bisphenol A in a solvent in the presence of a palladium/alkali metal catalyst in which palladium and an alkali metal are both supported on a carrier to obtain alicyclic diketones such as 2,2-bis(4-oxocyclohexyl)propane and 4,4′-bicyclohexanone. The other process for producing alicyclic monoketones according to the present invention comprises hydrogenating biphenols such as bis(4-hydroxyphenyl) in an organic solvent in the presence of a palladium catalyst in which 10 to 30% by weight of palladium is supported on a carrier to obtain alicyclic monoketones such as 4(4′-hydroxyphenyl)cyclohexanone. According to the present invention, alicyclic monoketones or alicyclic diketones can be obtained with high selectivity and in high yields through simple steps, because the process includes only one reaction step to hydrogenate substituted bisphenols under relatively mild conditions.
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- Amidino derivatives useful as nitric oxide synthase inhibitors
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The current invention discloses useful pharmaceutical compositions containing amidino derivative useful as nitric oxide synthase inhibitors.
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- Amidino dervatives useful as nitric oxide synthase inhibitors
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The current invention discloses useful pharmaceutical compositions containing azepine derivatives useful as nitric oxide synthase inhibitors.
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- Oligo(cyclohexylidene) oximes and derivatives as probe molecules for long-range substituent effects on13C NMR chemical shifts
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For a series of rodlike aliphatic oximes (1-4) the influence of the oxime substituent on the 13C NMR chemical shifts has been studied. Various 2D NMR techniques were applied for the unequivocal assignment of their 1H and 13C resonances. For bicyclohexylidene oximes 1-2 long-range substituent effects on the 13C NMR chemical shifts of aliphatic carbon atoms of the six-membered rings due to the presence of the oxime group are discernible up to positions six carbon-carbon bonds distant from the iminyl carbon! The 13C NMR data obtained for bicyclohexyl oximes 3-4 reveal that in this series the effect is limited to carbon atoms which are five bonds distant from the iminyl carbon. The observed differences between the two series is attributed to the presence of an olefinic double bond in 1-2, whch becomes polarized by the electric field of the oxime substituent.
- Hoogesteger, Frans J.,Grove, David M.,Jenneskens, Leonardas W.,De Bruin, Theodorus J. M.,Jansen, Bart A. J.
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p. 2327 - 2334
(2007/10/03)
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- Extractive hydrogenation: A new and versatile technique broadening gas chromatography applications
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A new technique, "extractive hydrogenation", is combined with gas chromatography (GC) to analyze organic including biological samples. In this method, the sample (or an extract thereof) is subjected to intense hydrogenation under aqueous conditions in the presence of excess (in terms of mass) palladium/carbon catalyst. Products with a saturated hydrocarbon framework result, for example, as alcohols, the larger of which adsorb onto the carbon of the catalyst. These larger products are separately recovered by extracting the washed catalyst with an organic solvent and then detected by GC. Here, the GC was fitted with a flame ionization detector (FID) or an electron impact mass spectrometer (EI-MS). Detection in this way (H2-GC) of the following trace analytes was achieved: (a) 100 μg of an (acetylamino)fluorene-deoxyguanosine DNA adduct spiked into 1 mg of DNA; (b) 1.5 μg of novobiocin, an antibiotic, spiked into 15 mL of milk (followed by extraction prior to H2-GC); and (c) 1 mg of 4-aminobiphenyl, a carcinogen, spiked into 150 mg of hemoglobin (followed by hydrolysis prior to H2-GC). The technique gave somewhat different GC-FID chromatograms for Escherichia coli and Enterococcus bacteria. Unlike pyrolysis (similarly used prior to GC), which tends to convert a biological sample into a char, the hydrogenation technique turns the sample into a clear aqueous solution. Most importantly, the method brings a broad variety of organic-containing samples in a simple way into the scope of GC/EI-MS with its computerized library of spectra.
- Itani, Mohammad,Giese, Roger W.
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p. 1189 - 1197
(2007/10/02)
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- A Convenient Preparation of Ketones by the Oxidation of Secondary Alcohols with Chromium(VI) Trioxide in Aprotic Solvent in the Presence of "Wet"-Aluminium Oxide
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The oxidation of aliphatic and alicyclic secondary alcohols with chromium(VI) trioxide in the presence of "wet"-aluminium oxide in hexane gave the corresponding ketones in excellent yields under mild conditions.
- Hirano, Masao,Nagasawa, Sonoko,Morimoto, Takashi
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p. 2857 - 2859
(2007/10/02)
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- CYCLIC HYDROCARBONS WITH AN AMINOALKYL SIDECHAIN
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Provided are cyclic hydrocarbons of Formula I with an aminoalkyl sidechain that are useful for treating phospholipase A2 mediated conditions, diabetes, and obesity.
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- A NEW PROCEDURE FOR DETHIOACETALIZATION
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A simple procedure has been developed for the conversion of thioacetals to the corresponding carbonyl compounds using the combination of phenyl dichlorophosphate, dimethylformamide and sodium iodide.
- Liu, Hsing-Jang,Wiszniewski, Virginia
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p. 5471 - 5474
(2007/10/02)
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- PHENYL DICHLOROPHOSPHATE AS AN ACTIVATING AGENT IN THE PFITZNER-MOFFATT OXIDATION
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Phenyl dichlorophosphate has been shown to be a highly efficient activating agent for dimethyl sulfoxide in the Pfitzner-Moffatt oxidation.Alcohols are readily converted to the corresponding ketones and aldehydes with this reagent under very mild conditions by a simple procedure.
- Liu, Hsing-Jang,Nyangulu, James M.
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p. 3167 - 3170
(2007/10/02)
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- Hydrogenation of 4-Substituted Biphenyls
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Hydrogenations of 4-hydroxy-(1a), 4-methoxy-, and 4-methylbiphenyls were carried out in the presence of Raney nickel (R-Ni), palladium-on-carbon (Pd-C), or platinum as catalysts under relatively mild conditions.The reaction rates depend primarily on the catalysts and less on the substrates.Hydrogenation with Pd-C or Pt took place predominantly in the phenyl ring, independent of the substituent.On the other hand, hydrogenation with R-Ni caused reduction mainly in the substituted aromatic ring.Hydrogenation of the phenol, 1a, using R-Ni afforded predominantly trans-4-phenylcyclohexanol in preference to the cis isomer, differing from the other reactions examined.
- Minabe, Masahiro,Watanabe, Kousuke,Ayabe, Yooichi,Yoshida, Masaaki,Toda, Takashi
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p. 1745 - 1748
(2007/10/02)
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- DIRECT CONVERSION OF SILYL ETHERS INTO CARBONYL COMPOUNDS WITH JONES REAGENT IN THE PRESENCE OF POTASSIUM FLUORIDE
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Treatment of silyl ethers with Jones reagent in acetone in the presence of potassium fluoride resulted in the silicon-oxygen bond cleavage and oxidation to give carbonyl compounds directly
- Liu, Hsing-Jang,Han, In-Sup
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p. 759 - 764
(2007/10/02)
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