cas 13674-16-3, 2-Hydroxy-3-phenylpropanoic acid methyl ester

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Tandem Wittig rearrangement/aldol reactions for the synthesis of glycolate aldols
A new tandem Wittig Rearrangement/aldol reaction of O-benzyl or O-allyl glycolate esters is described. This reaction generates two carbon-carbon bonds and two contiguous stereocenters in a single step from simple starting materials. The [1,2]-Wittig rearrangement proceeds under very mild reaction conditions that do not require the use of a strong base, and the 1,2-diol products are obtained in good yield with excellent diastereoselectivity (>20:1).
Bertrand, Myra Beaudoin,Wolfe, John P.
p. 4661 - 4663
(2006)
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Photoreduction of Keto Carboxylic Acid Derivatives to Oxyacid Derivatives Catalyzed by ZnTPPS-Quinolinium-3-carboxamide-CTAB Micelle
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Tabushi,Iwao,Kugimiya, Shin-ichi,Mizutani, Tadashi
p. 1658 - 1659
(1983)
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Photochemically induced coupling reaction of triarylstibines with olefins
Photoreaction of triarylstibines with styrenes resulted in the formation of 2-aryl-1-phenylethanols accompanied by air oxidation. Formation of the products has been explained by the valence expansion of the oxygen-antimony- styrene complex to a five-valent intermediate, followed by reductive coupling.
Kakusawa, Naoki,Tsuchiya, Takashi,Kurita, Jyoji
p. 9743 - 9746
(1998)
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Controllable Intramolecular Unactivated C(sp3)-H Amination and Oxygenation of Carbamates
Dual catalyst-controlled intramolecular unactivated C(sp3)-H amination and oxygenation of carbamates merging visible-light photocatalysis and earth-abundant transition metal catalysis have been reported. Useful amino alcohol and diol derivatives could be selectively obtained from readily available tertiary alcohol derivatives. The possible mechanisms have been proposed via a 1,5-HAT process followed by Lewis acid-controlled cyclization. The nickel and zinc catalysts inhibit the formation of oxygenation and amination products, respectively. An interesting phenomenon of chirality transfer is also observed.
Guo, Qihang,Ren, Xiang,Lu, Zhan
p. 880 - 884
(2019/05/16)

PROCESS OF PRODUCING ALPHA-HYDROXY COMPOUNDS AND USES THEREOF
New process of producing alpha-hydroxy compounds from sustainable resources useful as platform chemicals, such as hydroxy analogues of amino acids or polymer precursors.
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Page/Page column 20-22

(2019/08/29)

Mechanistic insight into catalytic aerobic chemoselective α-oxidation of acylpyrazoles
Mechanistic studies on catalytic aerobic chemoselective α-oxidation of acylpyrazoles, including control experiments, kinetic isotope effect experiments, and radical clock experiments, are described. The key to promoting the reaction was the in-situ genera
Taninokuchi, Seiya,Yazaki, Ryo,Ohshima, Takashi
p. 906 - 918
(2019/08/01)

PYRIDONE OR PYRIMIDONE DERIVATIVE, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF
Provided is a pyridone or pyrimidone derivative(s) represented by general formula (I) and its preparation method and use. Substituents of the compound of general formula (I) are defined the same as in the specification.
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Paragraph 0173; 0174; 0175

(2017/02/24)

Catalytic Aerobic Chemoselective α-Oxidation of Acylpyrazoles en Route to α-Hydroxy Acid Derivatives
Catalytic aerobic chemoselective α-oxidation of acylpyrazoles is described. Acylpyrazoles, carboxylic acid oxidation state substrates, were efficiently oxidized under aerobic conditions using TEMPO as an oxygenating agent. The mild catalytic conditions of the present catalysis were amenable to late-stage α-oxidation of various pharmaceutical agents and natural products, leading to previously unreported α-hydroxy acid derivatives in short steps. Preliminary mechanistic studies revealed that in situ generated copper(II) peroxo species served as a Lewis acid/Br?nsted base cooperative catalyst.
Taninokuchi, Seiya,Yazaki, Ryo,Ohshima, Takashi
p. 3187 - 3190
(2017/06/23)

Metal-free one-pot α-carboxylation of primary alcohols
An efficient metal-free procedure for the formal α-carboxylation of primary alcohols has been developed. The method involves a one-pot oxidation/Passerini/hydrolysis sequence and provides access to α-hydroxy acids bearing a broad range of functional groups. A minor modification to the reaction conditions extends the range of accessible products to α-hydroxy esters.
Van Der Heijden, Gydo,Kraakman, Jasper,Biemolt, Jasper,Ruijter, Eelco,Orru, Romano V. A.
p. 9716 - 9719
(2016/10/31)

Asymmetric transfer hydrogenation of α-azido acrylates
The asymmetric transfer hydrogenation of α-azido acrylates has been explored, a range of α-hydroxy esters are produced with good enantioselectivities (80-90% ee). The reaction was conducted in the wet HCO2H/NEt3 with Ru-TsDPEN A.
Ji, Yang,Xue, Ping,Ma, Dan-Dan,Li, Xue-Qiang,Gu, Peiming,Li, Rui
supporting information
p. 192 - 194
(2015/02/05)

Kinetic resolution of mandelate esters via stereoselective acylation catalyzed by lipase PS-30
By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic mandelate esters has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 197.5. Substituent effect is briefly discussed.
Chen, Peiran,Yang, Wenhong
p. 2290 - 2294
(2014/04/17)

Chemoselective esterification of α-hydroxyacids catalyzed by salicylaldehyde through induced intramolecularity
A new, direct and chemoselective esterification of α-hydroxyacids was developed using a reversible covalent-binding strategy. By taking advantage of acetal chemistry, simple aldehydes can be used to efficiently catalyze the esterification of α-hydroxy carboxylic acids in the presence of β-hydroxyacid moieties or other carboxylic acids in amounts equal to or in excess of the alcohols. A diverse array of α-aryl, α-alkyl, α-heteroaryl, and functionalized α-hydroxyacids were smoothly esterified with 1° and 2° alcohols catalyzed by 10 mol% inexpensive and commercially available salicylaldehyde, furnishing the resultant esterification products in 83-95% yields after a simple basic aqueous workup to remove the unreacted hydroxyacids. In addition, the salicylaldehyde can be recovered through vacuum distillation or silica gel purification, thereby meeting the standards of green chemistry. A mechanistic study proved that the formation of covalent adduct III during our proposed catalytic cycle (Scheme 1A) is responsible for the real catalysis.
Weng, Shiue-Shien,Li, Hsin-Chun,Yang, Teng-Mao
p. 1976 - 1986
(2013/03/13)

AuCl3/AgSbF6-catalyzed rapid epoxide to carbonyl rearrangement
An efficient epoxide to carbonyl rearrangement using catalytic AuCl 3/AgSbF6 has been presented. The reactions are fast and high yielding. β-Hydrogen migration takes place exclusively when hydrogen and methyl or substituted methyl groups are present at β-carbon of epoxide. When phenyl/acetyl/benzoyl and hydrogen are available at same carbon atom, migration of the former is preferred over the latter.
Gudla, Vanajakshi,Balamurugan, Rengarajan
p. 5243 - 5247
(2012/11/07)

Radical addition of arylboronic acids to various olefins under oxidative conditions
Arylboronic acids are shown to be valuable precursors for aryl radicals upon treatment with manganese triacetate. Under these oxidative conditions the intermediately generated aryl radicals undergo addition to olefins to give the arylhydroxylation products A in the presence of dioxygen. In the absence of dioxygen, for some olefins double olefin addition and subsequent homolytic aromatic substitution provide tetrahydronaphthaline derivatives B in moderate to good yields.
Dickschat, Arne,Studer, Armido
supporting information; experimental part
p. 3972 - 3974
(2010/11/02)

PALLADIUM CATALYSTS
The invention relates to a particulate substance comprising a particulate porous support coupled to a palladium species. The palladium species may comprise palladium nanoclusters. The particulate substance may be used as a catalyst for conducting a carbon-carbon coupling reaction or a reduction.
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Page/Page column 17; 19

(2010/05/13)

Palladium nanoclusters supported on propylurea-modified siliceous mesocellular foam for coupling and hydrogenation reactions
This paper describes the synthesis, characterization and applications of palladium (Pd) nanoparticles supported on siliceous mesocellular foam (MCF). Pd nanoparticles of 2-3 nm and 4-6 nm were used in reactions involving molecular hydrogen (such as hydrogenation of double bonds and reductive amination), transfer hydrogenation of ketones and epoxides, and coupling reactions (such as Heck and Suzuki reactions). They successfully catalyzed all these reactions with excellent yield and selectivity. This heterogeneous catalyst was easily recovered by filtration, and recycled several times without any significant loss in activity and selectivity. The palladium leaching in the reactions was determined to be much less than the FDA-approved limit of 5 ppm. Furthermore, the catalyst can be stored and handled under normal atmospheric conditions. This immobilized catalyst allows for ease of recovery/reuse and minimization of waste generation, which are of great interest in the development of green chemical processes.
Erathodiyil, Nandanan,Ooi, Samuel,Seayad, Abdul M.,Han, Yu,Lee, Su Seong,Ying, Jackie Y.
experimental part
p. 3118 - 3125
(2009/04/08)

Substituted indoles and methods of their use
The present invention relates generally to substituted indoles and methods of using them.
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Page/Page column 18

(2010/11/25)

New boron(III)-catalyzed amide and ester condensation reactions
In 1996, we reported that benzeneboronic acids bearing electron-withdrawing groups at the meta- or para-position are highly effective catalysts for the amide condensation reaction in less-polar solvents. In this paper, we report that N-alkyl-4-boronopyridinium halides are more effective catalysts than the previous ones in more polar solvents. N-Alkyl-4-boronopyridinium halides are effective not only for amide condensation between equimolar mixtures of carboxylic acids and amines but also for the esterification of α-hydroxycarboxylic acids in alcohol solvents. Furthermore, perchlorocatecholborane is more effective than areneboronic acids for the amide condensation of sterically demanding carboxylic acids. In addition, Lewis acid-assisted Br?nsted acid (LBA), which is prepared from a 1:2 M mixture of boric acid and tetrachlorocatechol, is effective for the Ritter reaction from alcohols and nitriles to amides.
Maki, Toshikatsu,Ishihara, Kazuaki,Yamamoto, Hisashi
p. 8645 - 8657
(2008/02/08)

Thiazolo-naphthyl acids
The present invention relates to thiazolo-naphthyl acids of the formula and methods of using them to modulate PAI-1 expression and to treat PAI-1 related disorders.
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Page/Page column 13-14

(2008/06/13)

Solvolysis of benzyl alcohols and ethers in 1,2-diols and application to a deprotection of benzyl ether-type protecting groups
Some kinds of benzyl alcohols and ethers react with 1,2-diols, such as ethylene glycol and propylene glycol, at 130-190°C to give 2-hydroxyethyl or 2-hydroxypropyl ethers. Application of this reaction to a deprotection of benzyl ether-type protecting groups, under neutral conditions, was also described. Copyright
Miyake, Hideyoshi,Fujimura, Masahiro,Tsumura, Takatsugu,Sasaki, Mitsuru
p. 778 - 779
(2007/10/03)

Highly chemoselective methylation and esterification reactions with dimethyl carbonate in the presence of NaY faujasite. The case of mercaptophenols, mercaptobenzoic acids, and carboxylic acids bearing OH substituents
In the presence of NaY faujasite, the reactions of dimethyl carbonate (DMC) with several ambident nucleophiles such as o- and p-mercaptophenols (1a,b), o- and p-mercaptobenzoic acids (2a,b), o- and p-hydroxybenzoic acids (3a,b), mandelic and phenyllactic acids (4, 5), have been explored under batch conditions. Highly chemoselective reactions can be performed: at 150 °C, compounds 1 and 2 undergo only a S-methylation reaction, without affecting OH and CO2H groups; at 165 °C, acids 3-5 form the corresponding methyl esters, while both their aromatic and aliphatic OH substituents are fully preserved from methylation and/or transesterification processes. Typical selectivities are of 90-98% and isolated yields of products (S-methyl derivatives and methyl esters, respectively) are in the range of 85-96%. A comparative study with K2CO3 as a catalyst is also reported. Although the base (K2CO3) turns out to be more active than the zeolite, the chemoselectivity is elusive: compounds 2a,b undergo simultaneous S-methylation and esterification reactions, and acids 3-5 yield complex mixtures of products of O-methylation, O-methoxycarbonylation, and esterification of their OH and CO2H groups, respectively. Overall, the combined use of a nontoxic reagent/solvent (DMC) and a safe promoter (NaY) imparts a genuine ecofriendly nature to the investigated synthesis.
Selva, Maurizio,Tundo, Pietro
p. 1464 - 1470
(2007/10/03)

N-alkyl-4-boronopyridinium halides versus boric acid as catalysts for the esterification of α-hydroxycarboxylic acids
(Chemical Equation Presented) Boric acid is a highly effective catalyst for the dehydrative esterification reaction between equimolar mixtures of α-hydroxycarboxylic acids and alcohols. In contrast, N-methyl-4- boronopyridinium iodide (2a) is a more effective catalyst than boric acid for the similar esterification in excess alcohol. A heterogeneous catalyst, such as N-polystyrene-bound 4-boronopyridinium chloride, is also an effective catalyst and can be recovered by filtration.
Maki, Toshikatsu,Ishihara, Kazuaki,Yamamoto, Hisashi
p. 5047 - 5050
(2007/10/03)

BIPHENYLOXY-ACIDS
The present invention relates generally to substituted biphenyloxy acids (such as 4'-aryl-amido-biphenyl--4(3)-yloxy-acids and 4’-aryl-amidomethyl-biphenyl-4(3)-yloxy-acids) and methods of using them.
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Page/Page column 51

(2008/06/13)

6-(Aryl-amido or aryl-amidomethyl)-naphthalen-2-yloxy-acidic derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1)
This invention provides novel compounds, pharmaceutical compositions and methods of treating thrombotic disorders in mammals, the compounds having the formula: Wherein: Ar is phenyl, naphthyl, furanyl, benzofuranyl, indolyl, pyrazolyl, oxazolyl, fluorenyl, phenylcycloalkane where the cycloalkane can be cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl and Ar can be optionally substituted by 1 to 3 groups selected from C1-C6 alkyl, C1-C6 alkoxy, hydroxy, phenyl-(CH2)0-6—, phenyl-(CH2)0-6O—, C3-C6 cycloalkyl, —(CH2)—C3-C6 cycloalkyl, halogen, C1-C3 perflouroalkyl and C1-C3 perfluoroalkoxy where phenyl can be substituted with from 1 to 3 groups selected from C1-C6 alkyl, C1-C6 alkoxy, phenyl, halogen, trifluoromethyl or trifluoromethoxy; R1 is hydrogen, C1-C6 alkyl or phenyl-(CH2)1-6— where phenyl can be substituted with C1-C6 alkyl, C1-C6 alkoxy, halo, trifluoromethyl or trifluoromethoxy; R2 and R3 are H, C1-C6 alkyl, phenyl-(CH2)0-3—, halo and C1-C3 perfluoroalkyl where phenyl can be substituted with C1-C6 alkyl, C1-C6 alkoxy, halo, trifluoromethyl or trifluoromethoxy; R4 is —CHR5CO2H or —CH2-tetrazole where R5 is H or benzyl; and n=0 or 1; or a pharmaceutically acceptable salt or ester form thereof.
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(2008/06/13)

Benzothiophenes, benzofurans, and indoles useful in the treatment of insulin resistance and hyperglycemia
This invention provides compounds of Formula I having the structure E is S, SO, SO2, O, or NR1c; X is hydrogen, halogen, alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, CN, aryl, aralkyl of 6-12 carbon atoms, hydroxyalkyl of 1-6 carbon atoms, hydroxyaralkyl of 6-12 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, aryloxy; arylalkoxy, nitro, amino, NR2R2a, NR2COR2a, cycloalkylamino of 3-8 carbon atoms, morpholino, alkylsulfanyl of 1-6 carbon atoms, arylsulfanyl, pyridylsulfanyl, 2-N,N-dimethylaminoethylsulfanyl, —OCH2CO2R2bor —COR2c; Z1and Z2are each, independently, hydrogen, halogen, CN, alkyl of 1-6 carbon atoms, aryl, aralkyl of 6-12 carbon atoms, cycloalkyl of 3-8 carbon atoms, nitro, amino, —NR1R1a, —NR1COR1a, cycloalkylamino of 3-8 carbon atoms, morpholino, or OR8, or Z1and Z2may be taken together as a diene unit having the formula —CH═CR9—CR10═CR11—; or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.
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(2008/06/13)

4-aryl-1-oxa-9-thia-cyclopenta[b]fluorenes
This invention provides compounds of Formula I having the structure wherein B and D are each, independently, hydrogen, halogen, -CN, alkyl of 1-6 carbon atoms, aryl, or aralkyl of 6-12 carbon atoms; R1 is hydrogen, alkyl of 1-6 carbon atoms, -CH(R2)W, -C(CH3)2CO2R3, 5-thiazolidine-2,4-dione, -CH(R4)CH2CO2R3, -COR3, or -PO3(R3)2; R2 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, aryl, -CH2(1H-imidazol-4-yl), -CH2(3-1H-indolyl), -CH2CH2(1,3-dioxo-1,3-dihydro-isoindol-2-yl), -CH2CH2(1-oxo-1,3-dihydro-isoindol-2-yl), or -CH2(3-pyridyl); W is -CO2R3, -CONH2, -CONHOH, -CN, CONH(CH2)2CN, 5-tetrazole, or -PO3(R3)2; R3 is hydrogen, alkyl of 1-6 carbon atoms, or aryl; R4 is hydrogen or alkyl of 1-6 carbon atoms; or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.
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(2008/06/13)

11-aryl-benzo[B]naphtho[2,3-D]furans and 11-aryl-benzo[B]naphtho[2,3-D]thiophenes useful in the treatment of insulin resistance and hyperglycemia
This invention provides compounds of Formula I having the structure wherein A is hydrogen, halogen, or OH; B and D are each, independently, hydrogen, halogen, CN, alkyl of 1-6 carbon atoms, aryl, aralkyl of 6-12 carbon atoms, nitro, amino or OR; R is hydrogen, alkyl of 1-6 carbon atoms, -COR1, -CH2CO2R1, -CH(R1a)CO2R1, or -SO2R1; R1 and R1a are each, independently, hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms or aryl; E is S, SO, SO2, O; X is hydrogen, halogen, alkyl of 1-6 carbon atoms, CN, perfluoroalkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, aryloxy, arylalkoxy of 6-12 carbon atoms, nitro, amino, alkylsulfanyl of 1-6 carbon atoms, arylsulfanyl, pyridylsulfanyl, 2-N,N-dimethylaminoethylsulfanyl, or -OCH2CO2R1b; R1b is hydrogen or alkyl of 1-6 carbon atoms; Y and Z are each, independently, hydrogen or OR2; R2 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, or -CH2CO2R3; R3 is hydrogen or alkyl of 1-6 carbon atoms; C is hydrogen, halogen or OR4; R4 is hydrogen, alkyl of 1-6 carbon atoms, -CH(R5)W, -C(CH3)2CO2R6, 5-thiazolidine-2,4-dione, -CH(R7)CH2CO2R6, -COR6, PO3(R6)2, or -SO2R6; R5 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl, aryl, CH2(1H-imidazol-4-yl), -CH2(3-1H-indolyl), -CH2CH2(1,3-dioxo-1,3-dihydro-isoindol-2-yl), -CH2CH2(1-oxo-1,3-dihydro-isoindol-2-yl), -CH2(3-pyridyl), or -CH2CO2H; W is -CO2R6, -CONH2, -CONHOH, CN, -CONH(CH2)2CN, 5-tetrazole, -PO3(R6)2, -CH2OH, or -CH2Br, -CONR6CHR7CO2R8, R6 is hydrogen, alkyl of 1-6 carbon atoms, aryl or aralkyl; R7 is hydrogen, alkyl of 1-6 carbon atoms, aryl or aralkyl; R8 is hydrogen, alkyl of 1-6 carbon atoms, aryl or aralkyl; or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.
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(2008/06/13)

1-aryl-dibenzothiophenes
This invention provides compounds of Formula I having the structure STR1 wherein: B and D are each, independently, hydrogen, halogen, --CN, alkyl of 1-6 carbon atoms, aryl, aralkyl of 6-12 carbon atoms; X is H, or halogen; R1 is hydrogen, alkyl
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(2008/06/13)

Regioselective deoxygenation of the cyclic thionocarbonates of 2,3- dihydroxy esters with magnesium in methanol
Deoxygenation of the cyclic thionocarbonates of 2,3-dihydroxy esters was mediated with magnesium in methanol, which provided a facile method for the synthesis of α-hydroxy esters.
Rho, Ho-Sik,Ko, Byoung-Seob
p. 2875 - 2880
(2007/10/03)

Almond oxynitrilase-catalyzed transformation of aldehydes is strongly influenced by naphthyl and alkoxy substituents
Different α- and β-substituted aldehydes have been submitted to the catalytic action of almond oxynitrilase (PaHNL), in order to explore the influence of a stereocenter already present in the substrate on the selectivity of this enzyme. The results indicate that naphthyl and alkoxy substituents in the α- and also in the β-position to the aldehyde group significantly influence the stereochemical outcome of the PaHNL-catalyzed transformation.
Roda, Gabriella,Riva, Sergio,Danieli, Bruno
p. 3939 - 3949
(2007/10/03)

Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols
α-Hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic α-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions.
Dalla, Vincent,Cotelle, Philippe,Catteau, Jean Pierre
p. 1577 - 1580
(2007/10/03)

Synthesis and phosphatase inhibitory activity of analogs of sulfircin
Analogs of sulfircin (1) were synthesized and tested for inhibitory activity against a panel of phosphatases. We attempted to optimize the potency and selectivity of sulfircin for Cdc25A by modifying three structural areas of the molecule. An anionic grou
Cebula, Regina E.,Blanchard, Jill L.,Boisclair, Michael D.,Pal, Kollol,Bockovich, Nicholas J.
p. 2015 - 2020
(2007/10/03)

Imidazole derivatives and their use as cytokine inhibitors
As cytokine inhibitors 2,4,5-triarylimidazole compounds and compositions for use as cytokine inhibitors.
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(2008/06/13)

Anomalous fluorinations of 3-aryl-2-hydroxypropanoic esters by diethylaminosulfur trifluoride (DAST)
Treatment of 3-aryl-2-hydroxypropanoic esters 8 with diethylaminosulfur trifluoride (DAST) gives considerable amounts of rearranged 2-aryl-3-fluoropropanoic esters 12 together with the expected products 11. The extent of rearrangement is dependent on solv
Haigh, David,Jefcott, Lee J.,Magee, Katherine,McNab, Hamish
p. 2895 - 2900
(2007/10/03)

Oxidation of α-acetoxy acetals with trichloroisocyanuric acid
α-Acetoxy acid methyl esters are prepared in excellent yields by treating aliphatic α-acetoxy dimethyl acetals with trichloroisocyanuric acid in DMF.
Benincasa,Grandi,Ghelfi,Pagnoni
p. 3463 - 3470
(2007/10/03)

Pd-catalysed regiospecific reductive ring opening of epoxides and glycidic esters
The regiospecific ring opening of epoxides was achieved by Pd-catalysed transfer hydrogenolysis using ammonium formate as hydrogen source.
Varghese,Sudalai,Iyer
p. 2267 - 2273
(2007/10/02)

CYCLIC RENIN INHIBITORS CONTAINING 2-SUBSTITUTED (3S,4S)-4-AMINO-5-CYCLOHEXYL-3-HYDROXY PENTANOIC ACID, 2-SUBSTITUTED (3S,4S)-5-CYCLOHEXYL-3,4-DI-HYDROXY PENTANOIC ACID OR 2-SUBSTITUTED (4S,5S)-5-AMINO-6-CYCLOHEXYL-4-HYDROXYHEXANOIC ACID OR ITS ANALOGS
Compounds of the formula STR1 are disclosed. These compounds inhibit the angiotensinogen-cleaving action of the natural proteolytic enzyme, renin, are useful in treating, preventing or managing renin-associated hypertension, hyperaldosteronism, congestive heart failure, and glaucoma.
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(2008/06/13)

CYCLIC RENIN INHIBITORS CONTAINING 3(S)-AMINO-4-CYCLOHEXYL-2(R)-HYDROXY-BUTANOIC ACID OR 4-CYCLO-HEXYL-(2R,3S)-DIHYDROXYBUTANOIC ACID OR RELATED ANALOGS
Compounds of the formula: STR1 are disclosed. These compounds inhibit the angiotensinogen-cleaving action of the natural proteolytic enzyme, renin, and are useful in treating, preventing or managing renin-associated hypertension, hyperaldosteronism, congestive heart failure, and glaucoma.
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(2008/06/13)

Cyclic renin inhibitors
Compounds of the formula: are disclosed. These compounds inhibit the angiotensinogen-cleaving action of the natural proteolytic enzyme, renin, and are useful in treating, preventing or managing renin-associated hypertension, hyperaldosteronism, congestive
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(2008/06/13)

PEPTIDYL BETA-AMINOACYL AMINODIOL CARBAMATES AS ANTI-HYPERTENSIVE AGENTS
Non-peptidyl compounds characterized generally as β-aminoacyl aminodiol carbamates are useful as renin inhibitors for the treatment of hypertension.
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(2008/06/13)

Macrocyclic lactones having renin inhibiting properties
Compounds of the formula:
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(2008/06/13)

Oxygenation of Silyl Enol Ethers and Silyl Ketene Acetals with Molecular Oxygen and Aldehyde Catalyzed by Nickel(II) Complex. A Convenient Method for the Preparation of α-Hydroxy Carbonyl Compounds
In the presence of a catalytic amount of nickel(II) complex, silyl enol ethers and silyl ketene acetals are smoothly oxygenated by the combined use of molecular oxygen and aldehyde to afford α-siloxy carbonyl compounds via possible intermediates, siloxy epoxides.And on treatment of the α-siloxy carbonyl compounds with potassium fluoride α-hydroxy carbonyl compounds are obtained in good to high yields.
Takai, Toshihiro,Yamada, Tohru,Rhode, Oliver,Mukaiyama, Teruaki
p. 281 - 284
(2007/10/02)

Chroman- and thiochroman-4-acetic acids useful in the treatment of diabetic complications
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(2008/06/13)

Enantioselectivity of carbonic anhydrase catalyzed hydrolysis of mandelic methyl esters
We report the first enantioselective hydrolysis of esters catalyzed by caebonic anhydrase.We found that mandelic methyl esters are good substrates for carbonic anhydrase.The R enantiomers are better substrates and enantiomeric excess values are moderate (40-51percent).
Chenevert, Robert,Letourneau, Martin
p. 314 - 316
(2007/10/02)

PEPTIDYL ALPHA-AMINOACYL AMINODIOL CARBAMATES AS ANTI-HYPERTENSIVE AGENTS
Non-peptidyl compounds characterized generally as aminoacyl aminodiol carbamates are useful as renin inhibitors for the treatment of hypertension.
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(2008/06/13)

α-HYDROXYLATION OF CARBOXYLIC ACIDS AND AMIDES USING BIS(TRIMETHYLSILYL)PEROXIDE
Bis(trimethylsilyl)peroxide is shown to react with enolate anions derived from carboxylic acids and amides to give the corresponding α-hydroxy derivatives.
Pohmakotr, Manat,Winotai, Chanchai
p. 2141 - 2146
(2007/10/02)

Reactions of α-Hydroxy Carbonyl Compounds with Azodicarboxylates and Triphenylphosphine: Synthesis of α-N-Hydroxy Amino Acid Derivatives
Reaction of aliphatic α-hydroxy esters with azodicarboxylates and triphenylphosphine in the presence of either CbzNHOCH2Ph or trOCNHOCH2Ph provides a direct route to protected α-N-hydroxy amino acids.Similar reactions with aromatic α-hydroxy carbonyl compounds and derivatives result in predominate oxidation to the corresponding α-oxo carbonyl derivatives.
Kolasa, Teodozyj,Miller, Marvin J.
p. 4978 - 4984
(2007/10/02)

A SYNTHON FOR CHIRAL GLYCOLATE ENOLATE (ROC-HCOOR'): A CAMPHOR-BASED OXAZOLINE
Alkylations of the anion (7a) derived from a camphor-based oxazoline proceed in good yield.Hydrolysis affords the corresponding α-hydroxy acids in high ee.
Kelly, T. Ross,Arvanitis, Argyrios
p. 39 - 42
(2007/10/02)