- Electrochemically driven desaturation of carbonyl compounds
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Electrochemical techniques have long been heralded for their innate sustainability as efficient methods to achieve redox reactions. Carbonyl desaturation, as a fundamental organic oxidation, is an oft-employed transformation to unlock adjacent reactivity through the formal removal of two hydrogen atoms. To date, the most reliable methods to achieve this seemingly trivial reaction rely on transition metals (Pd or Cu) or stoichiometric reagents based on I, Br, Se or S. Here we report an operationally simple pathway to access such structures from enol silanes and phosphates using electrons as the primary reagent. This electrochemically driven desaturation exhibits a broad scope across an array of carbonyl derivatives, is easily scalable (1–100 g) and can be predictably implemented into synthetic pathways using experimentally or computationally derived NMR shifts. Systematic comparisons to state-of-the-art techniques reveal that this method can uniquely desaturate a wide array of carbonyl groups. Mechanistic interrogation suggests a radical-based reaction pathway. [Figure not available: see fulltext.]
- Gnaim, Samer,Takahira, Yusuke,Wilke, Henrik R.,Yao, Zhen,Li, Jinjun,Delbrayelle, Dominique,Echeverria, Pierre-Georges,Vantourout, Julien C.,Baran, Phil S.
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p. 367 - 372
(2021/03/31)
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- Platinum-Catalyzed α,β-Desaturation of Cyclic Ketones through Direct Metal–Enolate Formation
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The development of a platinum-catalyzed desaturation of cyclic ketones to their conjugated α,β-unsaturated counterparts is reported in this full article. A unique diene-platinum complex was identified to be an efficient catalyst, which enables direct metal-enolate formation. The reaction operates under mild conditions without using strong bases or acids. Good to excellent yields can be achieved for diverse and complex scaffolds. A wide range of functional groups, including those sensitive to acids, bases/nucleophiles, or palladium species, are tolerated, which represents a distinct feature from other known desaturation methods. Mechanistically, this platinum catalysis exhibits a fast and reversible α-deprotonation followed by a rate-determining β-hydrogen elimination process, which is different from the prior Pd-catalyzed desaturation method. Promising preliminary enantioselective desaturation using a chiral-diene-platinum complex has also been obtained.
- Chen, Ming,Dong, Guangbin
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supporting information
p. 7956 - 7961
(2021/03/01)
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- Bidentate Nitrogen-Ligated I(V) Reagents, Bi(N)-HVIs: Preparation, Stability, Structure, and Reactivity
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Hypervalent iodine(V) reagents are a powerful class of organic oxidants. While the use of I(V) compounds Dess-Martin periodinane and IBX is widespread, this reagent class has long been plagued by issues of solubility and stability. Extensive effort has been made for derivatizing these scaffolds to modulate reactivity and physical properties but considerable room for innovation still exists. Herein, we describe the preparation, thermal stability, optimized geometries, and synthetic utility of an emerging class of I(V) reagents, Bi(N)-HVIs, possessing datively bound bidentate nitrogen ligands on the iodine center. Bi(N)-HVIs display favorable safety profiles, improved solubility, and comparable to superior oxidative reactivity relative to common I(V) reagents. The highly modular synthesis and in situ generation of Bi(N)-HVIs provides a novel and convenient screening platform for I(V) reagent and reaction development.
- Xiao, Xiao,Roth, Jessica M.,Greenwood, Nathaniel S.,Velopolcek, Maria K.,Aguirre, Jordan,Jalali, Mona,Ariafard, Alireza,Wengryniuk, Sarah E.
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p. 6566 - 6576
(2021/05/06)
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- CeO2-Supported Pd(II)-on-Au Nanoparticle Catalyst for Aerobic Selective α,β-Desaturation of Carbonyl Compounds Applicable to Cyclohexanones
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Direct selective desaturation of carbonyl compounds to synthesize α,β-unsaturated carbonyl compounds represents an environmentally benign alternative to classical stepwise procedures. In this study, we designed an ideal CeO2-supported Pd(II)-on-Au nanoparticle catalyst (Pd/Au/CeO2) and successfully achieved heterogeneously catalyzed selective desaturation of cyclohexanones to cyclohexenones using O2 in air as the oxidant. Besides cyclohexenones, various bioactive enones can also be synthesized from the corresponding saturated ketones under open air conditions in the presence of Pd/Au/CeO2. Preliminary mechanistic studies revealed that α-C-H bond cleavage in the substrates is the turnover-limiting step of this desaturation reaction.
- Jin, Xiongjie,Mizuno, Noritaka,Takei, Daisuke,Yabe, Tomohiro,Yamaguchi, Kazuya,Yatabe, Takafumi
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p. 5057 - 5063
(2020/05/27)
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- Enantioselective Synthesis of γ-Functionalized Cyclopentenones and δ-Functionalized Cycloheptenones Utilizing a Redox-Relay Heck Strategy
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In this report, the desymmetrization of cyclic enones under relay Heck conditions with an array of aryl boronic acids, alkenyl triflates and indole derivatives is described. This method grants facile access to diverse γ-functionalized cyclopentenones and δ-functionalized cycloheptenones. Using this approach, a formal synthesis of (S)-baclofen was completed in high yield and excellent enantioselectivity. (Figure presented.).
- Yuan, Qianjia,Prater, Matthew B.,Sigman, Matthew S.
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supporting information
p. 326 - 330
(2019/11/14)
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- Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones
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Selectivity between 1,2 and 1,4 addition of a nucleophile to an α,β-unsaturated carbonyl compound has classically been modified by the addition of stoichiometric additives to the substrate or reagent to increase their “hard” or “soft” character. Here, we demonstrate a conceptually distinct approach that instead relies on controlling the coordination sphere of a catalyst with visible light. In this way, we bias the reaction down two divergent pathways, giving contrasting products in the catalytic hydroboration of α,β-unsaturated ketones. This includes direct access to previously elusive cyclic enolborates, via 1,4-selective hydroboration, providing a straightforward and stereoselective route to rare syn-aldol products in one-pot. DFT calculations and mechanistic experiments confirm two different mechanisms are operative, underpinning this unusual photocontrolled selectivity switch.
- Beltran, Frédéric,Bergamaschi, Enrico,Funes-Ardoiz, Ignacio,Teskey, Christopher J.
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supporting information
p. 21176 - 21182
(2020/09/17)
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- Platinum-Catalyzed Desaturation of Lactams, Ketones, and Lactones
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The development of a general platinum-catalyzed desaturation of N-protected lactams, ketones, and lactones to their conjugated α,β-unsaturated counterparts is reported. The reaction operates under mildly acidic conditions at room temperature or 50 °C. It is scalable and tolerates a wide range of functional groups. The complementary reactivity to the palladium-catalyzed desaturation is demonstrated in the efficient conversion of iodide, bromide, and sulfur-containing substrates.
- Chen, Ming,Rago, Alexander J.,Dong, Guangbin
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supporting information
p. 16205 - 16209
(2018/11/23)
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- DIRECT B-ARYLATION OF CARBONYL COMPOUNDS
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Disclosed is a method for the β-C—H H functionalization of carbonyl compounds that is both selective and broadly applicable. The methods provide direct β-arylation of carbonyl compound with a diverse array of aryl or heteroaryl halides, aryl or heteroryl tosylate, aryl or heteroaryl triflates, or diaryliodonium salts, by palladium catalysis in the presence of a ligand and promoter.
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Paragraph 0122
(2016/09/12)
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- A highly efficient metal-free approach to: Meta - And multiple-substituted phenols via a simple oxidation of cyclohexenones
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A novel and efficient metal-free approach to substituted phenols has been disclosed from simple and readily available cyclohexenones and cyclohexenone equivalents. Dimethyl sulfoxide (DMSO), a simple and common organic reagent, was employed as a mild oxidant in this I2-catalysis, which significantly tolerates various substituents including some easily oxidizable or reducible functionalities. The challenging meta- and multiple-substituted phenols could be well prepared by this method. The metal-free and mild oxidation make this protocol very simple, practical, and easy to handle.
- Liang, Yu-Feng,Song, Song,Ai, Lingsheng,Li, Xinwei,Jiao, Ning
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supporting information
p. 6462 - 6467
(2018/06/08)
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- Aerobic double dehydrogenative cross coupling between cyclic saturated ketones and simple arenes
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The synthesis of 3-aryl-2-cyclohexenones is a topic of current interest as they are not only privileged structures in bioactive molecules, but they are also relevant feedstocks for the synthesis of substituted phenols or anilines, which are ubiquitous structural elements both in drug design and medicinal chemistry. A simple and sustainable one-pot aerobic double dehydrogenative reaction under mild conditions for the introduction of arenes in the β-position of cyclic ketones has been developed. Starting from the corresponding saturated ketone, this reaction sequence proceeds under relatively low Pd catalyst loading and involves catalytic amounts of electron-transfer mediators (ETMs) under ambient oxygen pressure. A simple and sustainable one-pot aerobic double dehydrogenative reaction under mild conditions for the introduction of arenes in the β-position of cyclic ketones has been developed (see scheme). Starting from the corresponding saturated ketone, this reaction sequence proceeds under relatively low Pd catalyst loading and involves catalytic amounts of electron-transfer mediators (ETMs) under ambient oxygen pressure.
- Gigant, Nicolas,Baeckvall, Jan-E.
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supporting information
p. 5890 - 5894
(2014/05/20)
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- Palladium-catalyzed saegusa-ito oxidation: Synthesis of α,β-Unsaturated carbonyl compounds from trimethylsilyl enol ethers
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Palladium-catalyzed Saegusa-Ito oxidation of trimethylsilyl enol ethers is possible using Oxone as a stoichiometric oxidant and sodium hydrogen phosphate as a buffer. Cyclic and acyclic enones as well as α,β-unsaturated aldehydes are obtained in good to excellent yields.
- Lu, Yingdong,Nguyen, Pierre Long,Levaray, Nicolas,Lebel, Heleine
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p. 776 - 779
(2013/02/25)
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- Synthesis of α,β-unsaturated carbonyl compounds via a visible-light-promoted organocatalytic aerobic oxidation
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α,β-Unsaturated ketones and aldehydes have been synthesized from their corresponding silyl enol ethers in a straightforward protocol involving a visible-light promoted organocatalytic, aerobic oxidation reaction. A cheap organic dye was used catalytically in these reactions as the photosensitizer.
- Zhang, Junlin,Wang, Leming,Liu, Qi,Yang, Zhen,Huang, Yong
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p. 11662 - 11664
(2013/12/04)
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- Vanadium phosphorus oxide modified by silver doping: A highly effective catalyst for allylic oxidation of cycloolefins
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Allylic oxidation of cycloolefins was carried out over Ag-VPO catalyst using tert-butyl hydroperoxide (TBHP) as oxidant in argon atmosphere, under our reaction conditions, attack of the activated C-H bonds was preferred instead of the epoxidation of C=C bond and corresponding α, β-enones were obtained as the main products. It is a high yielding, safe and eco-friendly method.
- Liu, Junhua,Wang, Fang,Ma, Zhenmao,Lin, Jun,Gu, Zhenggui
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experimental part
p. 103 - 107
(2012/03/09)
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- Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones
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α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. Here, we report the discovery and application of Pd(DMSO)2(TFA)2 as a catalyst for direct dehydrogenation of cyclohexanones and other cyclic ketones to the corresponding enones, using O2 as the oxidant. The substrate scope includes heterocyclic ketones and several natural-product precursors.
- Diao, Tianning,Stahl, Shannon S.
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supporting information; experimental part
p. 14566 - 14569
(2011/10/17)
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- DIPHENYL AZEPANE, DIAZEPANE AND OXAZEPANE DERIVATIVES AND USES THEREOF
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Compounds of the formula I: wherein m, n, X1, X2, Y1, Y2, R1 and R2 are as defined herein. Also provided are pharmaceutical compositions, methods of using, and methods of preparing the comp
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-
Page/Page column 17
(2011/06/24)
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- METHOD FOR PRODUCING CARBONYL COMPOUND AN PRO-OXIDANT USED FOR PRODUCTION OF CARBONYL COMPOUND
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The invention provides a process for the preparation of a carbonyl compound in high efficiency by oxidizing an alcohol. The process for the preparation of a carbonyl compound of the present invention includes a step of oxidizing an alcohol in the presence of a compound of the formula (I) or a derivative or a salt thereof, and an oxidant, wherein R1 and R2 independently represent hydrogen, a halogen, a nitro or acidic group, or an alkyl or alkoxy group, each of which optionally has a substituent, or R1 and R2 combine the two carbon atoms to which they are boned to form an aromatic ring.
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Page/Page column 15-16
(2009/08/16)
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- 2-iodoxybenzenesulfonic acid as an extremely active catalyst for the selective oxidation of alcohols to aldehydes, ketones, carboxylic acids, and enones with oxone
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Electron-donating group-substituted 2-iodoxybenzoic acids (IBXs) such as5-Me-IBX (1g), 5-MeO-IBX (1h), and 4,5-Me2-IBX were superior to IBX 1a as catalysts for the oxidation of alcohols with Oxone (a trad emark of DuPont) under nonaqueous conditions, although Oxone was almost insoluble in most organic solvents. The catalytic oxidation proceeded more rapidly and cleanly in nitromethane. Furthermore, 2-iodoxybenzenesulfonic acid (IBS, 6a) was much more active than modified IBXs. Thus, we established a highly efficient and selective method for the oxidation of primary and secondary alcohols to carbonyl compounds such as aldehydes, carboxylic acids, and ketones with Oxone in nonaqueous nitromethane, acetonitrile, or ethyl acetate in the presence of 0.05-5molpercentof 6a, which was generated in situ from 2-iodobenzenesulfonic acid (7a) or its sodium salt. Cycloalkanones could be further oxidized to α,β- cycloalkenones or lactones by controlling the amounts of Oxone under the same conditions as above. When Oxone was used under nonaqueous conditions, Oxone wastes could be removed by simple filtration. Based on theoretical calculations, we considered that the relatively ionic character of the intramolecular hypervalent iodine-OSO2 bond of IBS might lower the twisting barrier of the alkoxyperiodinane intermediate 16.
- Uyanik, Muhammet,Akakura, Matsujiro,Ishihara, Kazuaki
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supporting information; experimental part
p. 251 - 262
(2009/06/28)
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- Expedient synthesis and solvent dependent oxidation behavior of a water-soluble IBX derivative
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IBX derivative 6, synthesized in two steps from 2-aminoterephthalic acid, 8, is soluble in both DMF and water. A variety of alcohols are oxidized using 6 in DMF with ease and selectivity identical to that of parent IBX. However, oxidations carried out in water and other aqueous solvent mixtures using 6 exhibit unique selectivities toward different substrates and provide products different from reactions carried out in DMF. A mechanistic rationale is provided for this solvent dependent behavior of 6.
- Kommreddy, Amitha,Bowsher, Michael S.,Gunna, Meena R.,Botha, Kirankumar,Vinod, Thottumkara K.
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p. 4378 - 4382
(2008/12/21)
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- Palladium-catalyzed oxidation of cyclohexanones to conjugated enones using molecular oxygen
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Oxidation of cyclohexanones into conjugated enones with molecular oxygen as oxidant was achieved by palladium catalysts. A catalyst system consists of 1 mol % Pd(OCOCF3)2 and 5,5′-dimethyl-2,2′-bipyridine accomplished maximum 84% yield for the oxidation of cyclohexanone and 51-78% yields for 4-substituted-cyclohexanones.
- Tokunaga, Makoto,Harada, Saki,Iwasawa, Tetsuo,Obora, Yasushi,Tsuji, Yasushi
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p. 6860 - 6862
(2008/02/12)
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- One-pot β-substitution of enones with alkyl groups to β-alkyl enones
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Vinylic hydrogens at the β-position of enones were effectively substituted with alkyl groups in a one-pot procedure to afford β-alkyl enones in good to high isolated yields by conjugate addition of higher-order dialkyl cyanocuprates to enones, followed by a reaction with N-tert-butylbenzenesulfinimidoyl chloride at -78 °C. The Royal Society of Chemistry 2005.
- Matsuo, Jun-Ichi,Aizawa, Yayoi
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p. 2399 - 2401
(2007/10/03)
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- Indazole or indole derivatives, and use thereof in human medicine and more particularly in oncology
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The present invention relates to novel compounds derived from indazoles or indoles of formula (1) or formula (2), to methods for treating tumors or cancerous cells with compounds of formula (1) or formula (2) and to pharmacaetutical compositions comprisin
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- Pd-catalyzed carbonylative cross-coupling reactions by triorganoindiums: Highly efficient transfer of organic groups attached to indium under atmospheric pressure
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(Matrix presented) A highly atom-efficient synthetic method of unsymmetrical ketones was developed by using trialkyl- and triarylindiums, which could be employed as effective cross-coupling partners in Pd-catalyzed carbonylative cross-coupling reactions with a variety of organic electrophiles. The present method produced unsymmetrical ketones and 1,4-diacylbenzenes in good yields with highly efficient transfer of almost all the organic groups attached to the indium under atmospheric pressure of CO gas in THF at 66°C.
- Lee, Phil Ho,Lee, Sung Wook,Lee, Kooyeon
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p. 1103 - 1106
(2007/10/03)
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- Installation of carbon chain onto 2-cyclohexene-1,4-diol monoacetate
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Alkylation of cyclohexenyl monoacetate 1 with R2Cu(CN)(MgCl)2 or RMgBr/CuCN (cat.) in Et2O produced trans 1,2-isomers 4, while arylation and alkenylation of 1 was accomplished with lithium borates 5 and a nickel cat. to af
- Abbas, Ashraf A.,Kobayashi, Yuichi
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p. 119 - 122
(2007/10/03)
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- A new and one-pot synthesis of α,β-unsaturated ketones by dehydrogenation of various ketones with n-tert-butyl phenylsulfinimidoyl chloride
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α,β-Unsaturated ketones were synthesized by one-pot procedure from various ketones in good to excellent yields on treatment of their lithium enolates with N-tert-butyl phenylsulfinimidoyl chloride (1) under mild conditions.
- Mukaiyama, Teruaki,Matsuo, Jun-Ichi,Kitagawa, Hideo
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p. 1250 - 1251
(2007/10/03)
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- Efficient one-pot conversion of carbonyl compounds to their α,β-unsaturated derivatives using a recoverable, minimally fluorous organoselenium reagent
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(equation presented) A protocol for the preparation of a fluorous arylselenenyl chloride is described. This selenenyl chloride may be used for the direct α-selenation of ketones and, following oxidation and syn-elimination, formation of α,β-unsaturated carbonyl compounds. Treatment of the crude reaction mixtures with sodium metabisulfite reduces the various selenium species to the diaryl diselenide, which is then recovered in high yield by continuous fluorous extraction.
- Crich, David,Barba, Gregory R.
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p. 989 - 991
(2007/10/03)
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- Iron(III) mediated transformations of trimethylsilyloxy cyclopropyl ethers. Part 2: A new 4-substituted-2-cyclohexenone synthesis
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Conjugate addition of a variety of Grignard reagents to 2-cyclopentenone gave a number of silyl enol ethers (1) which were treated with Et2Zn/CH2I2 to give the corresponding cyclopropyl silyl ethers (2) in good yield. Ferric chloride ring expansion followed by base elimination of the resulting β-chloro ketones gave the 4-substituted-2-cyclohexenones (4) in moderate to good overall yield. The overall process provides a convenient three step route to these enones from 2-cyclopentenone.
- Booker-Milburn,Thompson
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p. 12955 - 12962
(2007/10/02)
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- Intramolecular Cooperative Reactions of 1,2-Bis(diazoketone)s. The First Syntheses of trans-Hydro-1H-2-inden-1-ones
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The intramolecular cooperative reactions of 1,2-bis(diazoketone)s initiated by the Wolff rearrangement of α-diazoketones have been investigated.Under thermal conditions, 1,2-bis(diazoketone)s are efficiently transformed into 2-cyclopenten-1-one derivatives with complete stereospecificity.Thus, a most extraordinary result is reported, that trans-hydro-2-inden-1-ones (1-3) were synthesized for the first time from trans-1,2-bis(diazoketone)s (5, 11, and 12), respectively.The unprecedented trans-hydroindenone structure was confirmed by X-ray analysis of 3 as well as 1H NMR analysis and was supported by ab initio molecular orbital calculations.The same reactions were also carried out under photochemical conditions and were applied to 1,3-bis(diazoketone)s, giving 2-cyclohexen-1-one derivatives.
- Nakatani, Kazuhiko,Takada, Kazunori,Isoe, Sachihiko
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p. 2466 - 2473
(2007/10/02)
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- A new 4-substituted-2-cyclohexenone synthesis
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Conjugate addition of a variety of Grignard reagents to 2-cyclopentenone followed by cyclopropanation of the resulting enol ethers gave a range of substituted cyclopropyl silyl ethers in good yield. Treatment of these cyclopropyl silyl ethers with ferric chloride in DMF gave the one carbon ring expanded β-chloro ketones which were eliminated to the corresponding 4-substituted-2-cyclohexenones.
- Booker-Milburn, Kevin I.,Thompson, David F.
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p. 7291 - 7294
(2007/10/02)
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- Novel Synthesis of trans-Hydroindenones by Thermal Reaction of α,ω-Bis(diazo)diketones
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Thermal reaction of α,ω-bis(diazo)diketones gives α,β-unsaturated cycloalkenones including unsubstituted trans-hydroindenones, which were difficult to access by the conventional synthetic reactions.
- Nakatani, Kazuhiko,Takada, Kazunori,Odagaki, Yoshihiko,Isoe, Sachihiko
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p. 556 - 557
(2007/10/02)
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- 1,5-DICARBONYL COMPOUNDS A GENERAL PREPARATION METHOD
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In this report, a general method for the preparation of 1,5-dicarbonyl compounds and six membered ring annelation is described.This method involves the reaction of hemiacetal vinylogs 1 with enol ethers 2 or 3 in the presence of a Lewis acid.This reaction was successfully applied to the enol ethers of α and α,α'-hindered ketones such as 2,2,6-trimethyl cyclohexanone. α-Cyperone and 6-epi-α-cyperone were obtained using this process.
- Duhamel, P.,Hennequin, L.,Poirier, J. M.,Tavel, G.,Vottero, C.
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p. 4777 - 4786
(2007/10/02)
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- SYNTHESIS OF CYCLOHEXYLALIPHATIC ACIDS AND THEIR PHARMACOLOGICAL PROPERTIES
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A series of substituted cyclohexylacetic acids I has been obtained by hydrogenation of the unsaturated analogues II and III.Esters of these analogues were prepared by the Horner-Wittig reaction of the corresponding cyclohexanones IV and/or 2-cyclohexenones V with triethyl phosphonoacetate.These esters were obtained in two isomeric forms (Z and E), differing in the double bond in the exo-position.The derivatives with a substituent in the 2-position exhibited a partial shift of the double bond to the cyclohexane ring; this shift was especially marked in the 2-phenyl derivative.With the acids I-III, activation of fibrinolysis was assessed by the hanging clot method; the anti-inflammatory effect was assessed by inhibition of two experimental model inflammations.The regression equation relating fibrinolytic capacity to lipophilicity was a quadratic one, the logarithm of optimum lipophilicity being log Popt = 5.55.A qualitative assessment of the anti-inflammatory effect in relation to lipophilicity suggests that log Popt is probably higher than with arylaliphatic acids.These acids seem to have an active site different from that of the acids I-III.
- Kuchar, Miroslav,Brunova, Bohumila,Grimova, Jaroslava,Vanecek, Stanislav,Holubek, Jiri
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p. 2896 - 2908
(2007/10/02)
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- The monoblocking of symmetrical diketones on insoluble polymer supports
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A 1 percent crosslinked divinylbenzene-styrene copolymer, incorporating vicinal diol groups or their isopropylidene precursors, was used to form the monoacetals of the symmetrical diketones, p-diacetylbenzene, 1,2-cyclohexanedione, 1,3-cyclohexanedione, 1,4-cyclohexanedione, and 2,5-hexanedione.The free ketone groups reacted with phenylmagnesium bromide to give, in high yield, after acid hydrolysis from the polymer, the expected products such as 3-phenyl-2-cyclohexen-1-one from 1,3-cyclohexanedione.The 13C nmr spectra of some polymer-bound substrates and simple analogs are described.
- Xu, Zhang-Huang,McArthur, Colin R.,Leznoff, Clifford C.
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p. 1405 - 1409
(2007/10/02)
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