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Rhodium-Catalysed Redox Isomerization of Hydroxy Alkynes to Trans Keto and Hydroxy Vinyl Esters. A Short and Stereoselective Synthesis of Dipeptide Isosters
Tris(triphenylphosphine)Rhodium(I) Chloride in the presence trialkyl phosphine catalyses the isomerization of hydroxy alkynes to unsaturated trans keto and hydroxy esters depending on the nature of the phosphine.Dipeptide isosters were obtained in an efficient manner by the application of this methodology.
Saiah, M. K. Eddine,Pellicciari, Roberto
p. 4497 - 4500
(1995)
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Catalytic Synthesis of 1 H-2-Benzoxocins: Cobalt(III)-Carbene Radical Approach to 8-Membered Heterocyclic Enol Ethers
The metallo-radical activation of ortho-allylcarbonyl-aryl N-arylsulfonylhydrazones with the paramagnetic cobalt(II) porphyrin catalyst [CoII(TPP)] (TPP = tetraphenylporphyrin) provides an efficient and powerful method for the synthesis of novel 8-membered heterocyclic enol ethers. The synthetic protocol is versatile and practical and enables the synthesis of a wide range of unique 1H-2-benzoxocins in high yields. The catalytic cyclization reactions proceed with excellent chemoselectivities, have a high functional group tolerance, and provide several opportunities for the synthesis of new bioactive compounds. The reactions are shown to proceed via cobalt(III)-carbene radical intermediates, which are involved in intramolecular hydrogen transfer (HAT) from the allylic position to the carbene radical, followed by a near-barrierless radical rebound step in the coordination sphere of cobalt. The proposed mechanism is supported by experimental observations, density functional theory (DFT) calculations, and spin trapping experiments.
De Bruin, Bas,De Zwart, Felix J.,Li, Zirui,Mathew, Simon,Wolzak, Lukas A.,Zhou, Minghui
supporting information
p. 20501 - 20512
(2021/12/03)

Copper-Catalyzed N-O Cleavage of α,β-Unsaturated Ketoxime Acetates toward Structurally Diverse Pyridines
The copper-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with 1,3-dicarbonyl compounds for the synthesis of three classes of structurally diverse pyridines has been developed. This method employs 1,3-dicarbonyl compounds as C2 synthons and enables the synthesis of multifunctionalized pyridines with diverse electron-withdrawing groups in moderate to good yields. The mechanistic investigation suggests that the reactions proceed through an ionic pathway.
Ding, Xiaojuan,Duan, Jindian,Fang, Zheng,Guo, Kai,Li, Zhenjiang,Mao, Yiyang,Rong, Binsen,Xu, Gaochen,Zhang, Lei,Zhu, Ning
supporting information
p. 2532 - 2542
(2020/03/13)

Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents
A series of novel (E)-4-oxo-2-crotonamide derivatives were designed and synthesized to find potent antituberculosis agents. All the target compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv(MTB). Results reveal that 4-phenyl moiety at part A and short methyl group at part C were found to be favorable. Most of the derivatives displayed promising activity against MTB with MIC ranging from 0.125 to 4 μg/mL. Especially, compound IIIa16 was found to have the best activity with MIC of 0.125 μg/mL against MTB and with MIC in the range of 0.05–0.48 μg/mL against drug-resistant clinical MTB isolates.
Ren, Jinfeng,Xu, Jian,Zhang, Guoning,Xu, Changliang,Zhao, LiLi,You, XueFu,Wang, Yucheng,Lu, Yu,Yu, Liyan,Wang, Juxian
p. 539 - 543
(2019/01/09)

Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones
(S)-2,15-Br2-DHTP-catalyzed asymmetric conjugate addition of boronic acids to β-trifluoromethyl α,β-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.
Chai, Guo-Li,Sun, A-Qiang,Zhai, Dong,Wang, Juan,Deng, Wei-Qiao,Wong, Henry N.C.,Chang, Junbiao
supporting information
p. 5040 - 5045
(2019/07/03)

A Catalytic Cross-Olefination of Diazo Compounds with Sulfoxonium Ylides
A ruthenium-catalysed cross-olefination of diazo compounds and sulfoxonium ylides is presented. Our reaction design exploits the intrinsic difference in reactivity of diazo compounds and sulfoxonium ylides as both carbene precursors and nucleophiles, which results in a highly selective reaction.
Neuhaus, James D.,Bauer, Adriano,Pinto, Alexandre,Maulide, Nuno
supporting information
p. 16215 - 16218
(2018/11/23)

A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water
A novel, hydrophilic and recyclable methoxypolyethylene glycol (PEG)-modulated s-triazine-based multifunctional Schiff base/N,P-ligand L9 was prepared and used in Pd-catalyzed Heck-type carbonylative coupling reactions, affording diverse chalcone derivatives and 1,4-dicarbonyl esters in good yields.
Gao, Pei-Sen,Zhang, Kan,Yang, Ming-Ming,Xu, Shan,Sun, Hua-Ming,Zhang, Jin-Lei,Gao, Zi-Wei,Zhang, Wei-Qiang,Xu, Li-Wen
supporting information
p. 5074 - 5077
(2018/05/26)

Potassium 2-oxo-3-enoates as Effective and Versatile Surrogates for α, β-Unsaturated Aldehydes in NHC-Catalyzed Asymmetric Reactions
Potassium 2-oxo-3-enoates, which are readily prepared at scale and easily stored, have been found to be effective and versatile surrogates for α,β-unsaturated aldehydes in NHC-catalyzed asymmetric reactions. Promoted by chiral N-heterocyclic carbenes combined with LiCl, these easy-to-handle solid salts could release of CO2 and then undergo asymmetric reactions via homoenolate and α, β-unsaturated acyl azolium intermediate. The reactions have broad substrate scopes with high enantioselectivities. (Figure presented.).
Gao, Yaru,Ma, Yafei,Xu, Chen,Li, Lin,Yang, Tianjian,Sima, Guoqing,Fu, Zhenqian,Huang, Wei
supporting information
p. 479 - 484
(2017/12/26)

Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study
Protein kinase B (PknB) is an essential serine/threonine protein kinase required for Mycobacterium tuberculosis (M. tb) cell division and cell-wall biosynthesis. A high throughput screen using PknB identified a (E)-4-oxo-crotonic acid inhibitor, named YH-8, which was used as a scaffold for SAR investigations. A significant improvement in enzyme affinity was achieved. The results indicated that the α,β-unsaturated ketone scaffold and “trans-” configuration are essential for the activity against PknB. And compounds with an aryl group, especially with electron-withdrawing substituents on benzene ring, exhibited four fold potency than that of YH-8.
Xu, Changliang,Bai, Xiaoguang,Xu, Jian,Ren, Jinfeng,Xing, Yun,Li, Ziqiang,Wang, Juxian,Shi, Jingjing,Yu, Liyan,Wang, Yucheng
p. 4763 - 4775
(2017/02/05)

Base-Controlled Reactions through an Aldol Intermediate Formed between 2-Oxoaldehydes and Malonate Half Esters
A practical, atom-economical, base-directed, and highly efficient method for the generation of different selective products through a common aldol intermediate of 2-oxoaldehydes and malonate half esters is successfully developed. The addition of a strong basic environment (potassium tert-butoxide) catalyzed the synthesis of stable decarboxylative aldol products (α-hydroxy ketones), while the Doebner modification procedure resulted in decarboxylative elimination to (E)-α,β-unsaturated esters in good yields. The application of this method in one pot and one pot/two steps with azoles helped to develop regioselective α- and β-azolated products in appreciable yields.
Kumar, Atul,Khan, Shahnawaz,Ahmed, Qazi Naveed
supporting information
p. 4730 - 4733
(2017/09/22)

Efficient synthesis of functionalized olefins by Wittig reaction using Amberlite resin as a mild base
A convenient procedure for the synthesis of olefins by the reaction of stabilized, semistabilized, and nonstabilized phosphorous ylides with various aldehydes or ketone using Amberlite resin as a mild base is described. Our developed method offers facile and racemization-free synthesis of α,β-unsaturated amino esters and chiral allylic amine. The developed methodology offers mild reaction conditions, high efficiency, and facile isolation of the final products, a practical alternative to known procedures.
Valkute, Tushar R.,Aratikatla, Eswar K.,Bhattacharya, Asish K.
p. 581 - 589
(2017/03/15)

Substrate-Controlled, One-Pot Synthesis: Access to Chiral Chroman-2-one and Polycyclic Derivatives
Based on the appropriate choice of electrophiles, one-pot, multicomponent, enantioselective domino reactions have been realized which contain a five-step sequence and provide highly efficient access to potentially bioactive chroman-2-one derivatives as a single diastereoisomer with excellent enantioselectivities and in high yields. This new strategy could significantly improve the previous protocol by directly starting from commercial 2-hydroxybenzaldehydes rather than preformed lactols, which have to be synthesized in several additional steps. (Chemical Equation Presented).
Sun, Xue-Li,Chen, Ying-Han,Zhu, Dan-Yang,Zhang, Yan,Liu, Yan-Kai
supporting information
p. 864 - 867
(2016/03/04)

Synthesis of 1,5-benzodiazepine derivatives using p-toluenesulfonic acid as catalyst
A series of substituted ethyl 4-oxo-4-phenylbut-2-enoates were prepared and reacted with substituted o-phenylenediamine, undergone Michael addition reactions and cyclodehydration to provide novel 4-phenyl-2,3-dihydro-1,5-benzodiazepine-2-carboxylate derivatives with excellent yields. The synthetic protocol fulfilled many green-chemical requirements by using simple catalyst p-toluenesulfonic acid as activator and ethanol as solvent at room temperature.
Wang, Shasha,Hu, Lijuan,Cheng, Suyan,Wang, Lanzhi
p. 419 - 424
(2015/01/30)

Structure-activity relationship, cytotoxicity and mode of action of 2-ester-substituted 1,5-benzothiazepines as potent antifungal agents
Our studies examined the structural features responsible for the antifungal activity of 2-ethoxycarbonyl-1,5-benzothiazepine (7a). Three series of 1,5-benzothiazepine derivatives were synthesized and screened for their antifungal activity. The results suggested that the ethoxycarbonyl group at the 2 position and the imine moiety on the seven-membered ring are essential for activity. The most potent of the synthesized analogues (7a, 7b) were further studied by evaluating their cytotoxicity and mode of action (for 7a). The results showed that compounds 7a and 7b were relatively safe for BV2 cells, but compound 7a interfered with Cryptococcus neoformans cell wall integrity by increasing the chitinase activity. Therefore, compound 7a was considered safe as an antifungal agent for animal cells. Three series of 1,5-benzothiazepine derivatives were synthesized and their antifungal activities were evaluated to determine the structure-activity relationships with respect to the antifungal activity of 2-ester-substituted 1,5-benzothiazepines. The effective antifungal compounds 7a and 7b were further studied for their antifungal activity, cytotoxicity and mechanism of action (for compound 7a). The results provided important information about this class of benzothiazepines. Copyright
Kang, Wang,Du, Xingqiong,Wang, Lanzhi,Hu, Lijuan,Dong, Yuhuan,Bian, Yanqing,Li, Yuan
p. 1305 - 1314
(2013/11/06)

Flow chemistry synthesis of zolpidem, alpidem and other GABAA agonists and their biological evaluation through the use of in-line frontal affinity chromatography
The flow of information between chemical and biological research can present a bottleneck in pharmaceutical research. Tools that bridge these disciplines and aid information exchange have therefore clear value. Over the last few years, both synthetic chemistry and biological screening have benefited from automation, and a seamless chemistry-biology interface is now possible. We report here on the use of flow processes to perform synthesis and biological evaluation in an integrated manner. As proof of concept, a flow synthesis of a series of imidazo[1,2-a]pyridines, including zolpidem and alpidem, was developed and connected to a Frontal Affinity Chromatography screening assay to investigate their interaction with Human Serum Albumin (HSA). The Royal Society of Chemistry 2013.
Guetzoyan, Lucie,Nikbin, Nikzad,Baxendale, Ian R.,Ley, Steven V.
p. 764 - 769
(2013/03/14)

Catalytic oxidations of enolizable ketones using 2-alkylidene-4- oxothiazolidine vinyl bromide
Direct oxidation of enolizable ketones to α-hydroxy derivatives, vicinal dicarbonyls or tricarbonyl compounds has been achieved by a catalytic amount of 2-alkylidene-4-oxothiazolidine vinyl bromide in DMSO as a solvent. The yields range from moderate to good.
Baranac-Stojanovi?, Marija,Markovi?, Rade,Stojanovi?, Milovan
experimental part
p. 8000 - 8008
(2011/11/06)

Efficient oxidation-Wittig olefination-Diels-Alder multicomponent reactions of α-hydroxyketones
α-Hydroxyketones undergo efficient tandem oxidation-Wittig olefination reactions in the presence of an oxidant to produce high yields of γ-ketocrotonate products. On carrying out the oxidation-Wittig olefination reaction in the presence of 2,3-dimethyl-1,3-butadiene, a novel multicomponent reaction sequence provides access to cycloadducts in high yield.
Harris, Geraint H.,Graham, Andrew E.
experimental part
p. 6890 - 6892
(2011/03/18)

Design, synthesis and conformational analysis of turn inducer cyclopropane scaffolds: microwave assisted amidation of unactivated esters on catalytic solid support to obtain γ-turn mimic scaffolds
Novel constrained 1-aroyl-cyclopropane-2,3-cis-dicarboxylic acid bis-[(2-hydroxy-ethyl)-amides] (17a-e) with varied torsional angles have been synthesized in high yield from unactivated esters of 1-aroyl-2,3-cis-diethoxycarbonylcyclopropanes (15a-e) on a catalytic solid support with reduced reaction times by using the monomode-microwave irradiation; 15a-e were obtained by diastereoselective ethoxycarbonylmethylene transfer from a sulfur ylide to ethyl β-aroylacrylates (10a-e). Torsional angles and interatomic distance measurements on the energy minimized structures of the obtained molecules (17a-e, DFT, B3LYP/6-31G* level) have established these molecules as valuable γ-turn mimic scaffolds.
Bhella, Surinderjit Singh,Elango, Munusamy,Ishar, Mohan Paul S.
experimental part
p. 240 - 246
(2009/04/06)

Catalytic reactions of carbene precursors on bulk gold metal
Bulk gold metal powder, consisting of particles (5-50 μm) much larger than nanoparticles, catalyzes the coupling of carbenes generated from diazoalkanes (R2C=N2) and 3,3-diphenylcyclopropene (DPCP) to form olefins. It also catalyzes cyclopropanation reactions of these carbene precursors with styrenes. The catalytic activity of the gold powder depends on the nature of the gold particles, as determined by TEM and SEM studies. The reactions can be understood in terms of mechanisms that involve the generation of carbene R2C: intermediates adsorbed on the gold surface.
Zhou, Yibo,Trewyn, Brian G.,Angelici, Robert J.,Woo, L. Keith
experimental part
p. 11734 - 11743
(2009/12/08)

Catalytic conjugate addition of indoles to 4-aryl-4-oxobut-2-enoates by FeCl3
The conjugate addition of indoles to 4-aryl-4-oxobut-2-enoates was achieved with FeCl3 as a catalyst under mild conditions. The reaction was highly regioselective and afforded a variety of new 3-substituted indoles in good to excellent yields. Copyright
Wang, Xiaoxia,Zhang, Yaohong,Xiao, Xiaohui,Li, Xinsheng
supporting information; experimental part
p. 1284 - 1285
(2009/12/03)

Base-catalyzed stereoselective isomerization of electron-deficient propargylic alcohols to E-enones
We have developed highly stereoselective methods to isomerize electron-deficient propargylic alcohols to E-enones under mild conditions (EWG = electron-withdrawing group). Among weak bases we screened, catalytic (10-20 mol %) 1,4-diazabicyclo[2.2.2]octane (DABCO) was found to be effective in most cases. When the substrate is conjugated with an amide, the addition of sodium acetate catalyzed the isomerization.
Sonye, John P.,Koide, Kazunori
p. 6254 - 6257
(2007/10/03)

The synthesis and application of 3,6-bis(triphenylphosphonium) cyclohexene dichromate: An efficient oxidizing agent
The synthesis of 3,6-bis(triphenylphosphonium) cyclohexene dichromate is described. This reagent oxidizes primary and secondary alcohols to their corresponding carbonyl compounds thiols to disulfides, and amines to their azo compounds. Copyright Taylor & Francis Group, LLC.
Badri, Rashid,Mostoufi, Azar
p. 1513 - 1519
(2007/10/03)

Two variations of solvent-reduced wittig olefination reactions - Comparison of solventless wittig reactions to wittig reactions under ultrasonication with minimal work-up
Stabilized and semi-stabilized phosphoranes can be subjected to solventless Wittig reactions with carbaldehydes. Simple heating of a mixture of added components at 100°C in an electric oven gives the corresponding olefins in good yield. Alternatively, the Wittig reactions can be carried out in a biphasic medium under ultrasonication. In this case, the Wittig products can be isolated by simple evaporation of the organic phase without additional work-up.
Watanabe, Masataka,Morais, Goreti Ribeiro,Mataka, Shuntaro,Ideta, Keiko,Thiemann, Thies
p. 909 - 915
(2007/10/03)

Selective oxidation of benzylic substrates to their corresponding carbonyl compounds with 3,6-Bis(triphenylphosphonium)cyclohexene peroxodisulfate
3,6-Bis(triphenylphosphonium)cyclohexene peroxodisulfate (BTPCP) was found to be a highly effective and selective oxidant for the conversion of benzyl monohalides, nitrils, and amines to their corresponding carbonyl compounds under mild and neutral conditions.
Badri, Rashid,Soleymani, Mousa
p. 1325 - 1332
(2007/10/03)

Zinc carbenoid-mediated chain extension: Preparation of α,β-unsaturated-γ-keto esters and amides
An efficient one-pot preparation of α,β-unsaturated-ω-keto esters and amides has been developed. A zinc carbenoid-mediated chain extension of a β-dicarbonyl substrate provides access to an intermediate zinc enolate, which is treated sequentially with a halogen and amine base. This method has been applied to a variety of ester and amide starting materials, as well as to amino acid-derived substrates and to a formal synthesis of (R,R)-(-)-pyrenophorin.
Ronsheim, Matthew D.,Zercher, Charles K.
p. 4535 - 4538
(2007/10/03)

3,6-bis(triphenylphosphonium) cyclohexene peroxodisulfate as an efficient and mild oxidizing agent for conversion of alkylbenzenes to corresponding carbonyl compounds
Oxidation of a series of alkylbenzenes by BTPCP under neutral conditions to corresponding carbonyl compounds is described.
Badri, Rashid,Soleymani, Mousa
p. 2385 - 2389
(2007/10/03)

A comparison of Wittig and Wittig Horner (wadsworth emmons) reagents in reactions with some α-dicarbonyl compounds
For the α-dicarbonyl compounds RCOCHO studied where R=H, Me or Ph it was found that the use of Wittig reagents resulted in higher overall yields of the expected products and that with neither type of reagent could the product OCHCH=CHCO2Et from glyoxal be isolated.
Mawaziny, Sheila,Makky, Sadiah
p. 61 - 69
(2007/10/03)

Stereospecific Stille-coupling reaction of (Z)-1,2- bis(trimethylstannyl)ethenes with hypervalent iodonium salts
The Stille coupling of (Z)-1,2-bis(trimethylstannyl)ethenes with hypervalent iodonium salts (1 equiv) proceeded stereospecifically in the presence of PdCl2 (5 mol %) in DMF at room temperature to afford partially substituted (Z)-vinylstannanes under mild conditions. Alternatively, the use of 2 equivalents of hypervalent iodonium salts afforded tri-substituted alkenes.
Kang, Suk-Ku,Lee, Yong-Tack,Lee, Sang-Ho
p. 3573 - 3576
(2007/10/03)

Reaction of phenyl- and alkoxycarbonylmethanesulfonyl fluoride with activated haloalkanes
Arylmethanesulfonyl fluorides condense with α-bromoketones by attacking at the methylenyl carbon instead of the carbonyl bond to give α,β-conjugated ketones.They also condense with other activated haloalkanes in a similar manner.The preparation of FSO2CH2R (R = CO2Me, CO2Et, CN) is described.Fluorosulfonyl acetate reacts with the carbonyl bonds of aldehydes to give alkenes, whereas it attacks the phenacyl bromide exclusively at the α-carbon.The reaction mode of these sulfonyl fluorides is discussed on the basis of kinetic data. Key words: α-Fluorosulfonylcarbanions; α,β-conjugated ketone; α,β-conjugated ester; alkene formations.
Kagabu, S.,Shimizu, C.,Takahashi, J.,Hara, K.,Koketsu, M.,Ishida, M.
p. 435 - 439
(2007/10/02)

Process for preparing trans-β-benzoylacrylic acid ester
A process for preparing trans-β-benzoylacrylic acid ester having the general formula (I): STR1 wherein R is alkyl group or aralkyl group, which comprises dealcoholizing β-benzoyl-α-alkoxypropionic acid ester having the general formula (II): STR2 wherein R is above, in the presence of an acid catalyst to give trans-β-benzoylacrylic acid ester having the general formula (I).According to the process of the present invention, the by-product (II) produced in the esterification reaction of β-benzoylacrylic acid (III) with the alcohol (V) by the dehydration reaction can be converted into the compound (I) by the dealcoholization reaction in the presence of the acid catalyst and thus trans-β-benzoylacrylic acid ester (I) with a high purity can be produced in an industrially advantageous manner.
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(2008/06/13)

Process for preparing trans-beta-benzoylacrylic acid ester
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(2008/06/13)

A CONVENIENT SYNTHESIS OF γ-OXO-ACRYLATES
Ethyl 2,4-dioxoalkanoates react chemoselectively with pyrrolidine acetate at the more electrophilic C-2 carbonyl, producing enaminone esters which on reduction with NaCNBH3 followed by pyrrolidine elimination, were transformed into γ-oxo-acrylates.
Manfredini, S.,Simoni, D.,Zanirato, V.,Casolari, A.
p. 3997 - 4000
(2007/10/02)

ORGANOPHOSPHORUS CHEMISTRY 10. THE BEHAVIOUR OF β-AROYLACRYLIC ACIDS TOWARD NUCLEOPHILIC PHOSPHORUS COMPOUNDS
The reaction of alkyl phosphites and thiolphosphoric acids with β-aroylacrylic acids 1a,b has been investigated.Dialkyl phosphites (DAP) attacked 1 at the β-carbon atom with respect to the aroyl-carbonyl function, to give phosphonate 1:1 adducts assigned structure 2A.Thiolphosphoric acids (7) attacked 1 at the same centre to give adducts 8.On the other hand, trialkyl phosphites (TAP) converted 1 into the respective esters 5, almost exclusively.Structures of the new products were assigned according to consistent analytical and spectroscopic measurements.Key words: β-aroylacrylic acids; alkylation; phosphorylation; thiophosphorylation.
Mahran, Mohamed R.,Abdou, Wafaa M.,Ganoub, Neven A. F.,Sidky, Mahmoud M.
p. 19 - 26
(2007/10/02)

Studies on antirheumatic agents: 3-benzoylpropionic acid derivatives
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Kameo,Ogawa,Takeshita,Nakaike,Tomisawa,Sota
p. 2050 - 2060
(2007/10/02)

THE REACTION OF ALKYL 4-HYDROXY-2-ALKYNOATES AND 4-HYDROXY-2-ALKYN-1-ONES WITH PALLADIUM TRIBUTYLAMMONIUM FORMATE AND WITH TRIBUTYLAMINE: PREPARATION OF 1,4-DICARBONYL COMPOUNDS
Ethyl 4-oxo-2-alkenoates and 1,4-dioxo-2-alkenes are easily prepared by treating ethyl 4-hydroxy-2-alkynoates and 4-hydroxy-2-alkyn-1-ones with n-tributylamine.Treatment of ethyl 4-hydroxy-2-alkynoates and 4-hydroxy-2-alkyn-1-ones with palladium-tributylammonium formate produces ethyl 4-oxo-alkanoates and 1,4-alkandiones in good to high yield through a novel one-pot isomerization/hydrogenation reaction.
Arcadi, A.,Cacchi, S.,Marinelli, F.,Misiti, D.
p. 1457 - 1460
(2007/10/02)

NAD(P)H MODELS 20 CHEMOSELECTIVE METAL ION CATALYZED REDUCTION OF α-KETO-β,γ-UNSATURATED ESTERS BY 1,4-DIHYDROPYRIDINE DERIVATIVES
Ethyl 2-oxo-4-aryl-3-butene-1-oates (1a-c) are reduced by NAD(P)H models (1-n-propyl-1,4-dihydronicotinamide (4) and Hantzsch ester (5)), in presence of magnesium perchlorate.One equivalent of the reductant reduces the substrates selectively to the corresponding 2-oxo-4-arylbutanoates (6, 10a, b).An additional equivalent and higher temperature, converts ethyl 2-oxo-4-phenylbutanoate (6) to ethyl 2-hydroxy-4-phenylbutanoate (7).Reduction of ethyl 2-oxo-4-phenyl-3-buten-1-oate (1a) by Hantzsch ester in C2H5OD or by Hantzsch ester-4,4-d2 in C2H5OH, leads to direct transfer of the hydrogen or deuterium, respectively, without isotopic scrambling.These results have been interpreted to support the hydride transfer mechanism.
Meijer, Louis H. P.,Pandit, Upendra K.
p. 467 - 472
(2007/10/02)

SYNTHESIS AND SOME TRANSFORMATIONS OF VINYL β-ACETYL- AND β-BENZOYLACRYLATES
Vinyl β-acetyl- and β-benzoylacrylates were obtained by transvinylation with vinyl acetate in the presence of the catalyst Hg(OCOCH3)2.BF3.O(C2H5)2.It was shown that the reactions with bromine, mercuric acetates, and butyl hydrosulfide at the vinyloxy group are regioselective.
Komarova, L. I.,Zhuravlev, S. V.,Sal'nikova, L. V.
p. 1422 - 1425
(2007/10/02)