- New route to enantiomers of cyclic β-hydroxyethers. The crystal structure of (S)-(+)-tetrahydrofurfuryl-O,O'-diacetyl-(2R,3R)-hydrogentartrate
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Title compounds 1-2 were readily resolved into their enantiomers by crystallizing their half esters formed with O,O'-diacetyl-(2R,3R)-tartaric acid. An intermolecular H-bond between the free carboxyl group and the ring oxygen, determined by single crystal X-ray study of (S)-(+)-tetrahydrofurfuryl-O,O'-diacetyl-(2R,3R)-hydrogentartrate, enhances the selectivity and the crystallizing ability itself.
- Mravik, Andras,Boecskei, Zsolt,Keszei, Sandor,Elekes, Ferenc,Fogassy, Elemer
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-
Read Online
- The discovery of a potent and selective pyrazolo-[2,3-e]-[1,2,4]-triazine cannabinoid type 2 receptor agonist
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The development of selective CB2 receptor agonists is a promising therapeutic approach for the treatment of inflammatory diseases, without CB1 receptor mediated psychoactive side effects. Preliminary structure-activity relationship studies on pyrazoylidene benzamide agonists revealed the -ylidene benzamide moiety was crucial for functional activity at the CB2 receptor. A small library of compounds with varying linkage moieties between the pyrazole and substituted phenyl group has culminated in the discovery of a potent and selective pyrazolo-[2,3-e]-[1,2,4]-triazine agonist 19 (CB2R EC50 = 19 nM, CB1R EC50 > 10 μM). Docking studies have revealed key structural features of the linkage group that are important for potent functional activity.
- Moir, Michael,Lane, Samuel,Montgomery, Andrew P.,Hibbs, David,Connor, Mark,Kassiou, Michael
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- C-2 auxiliaries for stereoselective glycosylation based on common additive functional groups
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The stereoselective introduction of the glycosidic bond is one of the main challenges in chemical oligosaccharide synthesis. Stereoselective glycosylation can be achieved using neighbouring group participation of a C-2 auxiliary or using additives, for example. Both methods aim to generate a defined reactive intermediate that reacts in a stereoselective manner with alcohol nucleophiles. This inspired us to develop new C-2 auxiliaries based on commonly used additive functionalities such as ethers, phosphine oxides and tertiary amides. Good 1,2-trans-selectivity was observed for the phosphine oxide and amide-based auxiliaries expanding the toolbox with new auxiliaries for stereoselective glycosylation reactions.
- Boltje, Thomas J.,De Kleijne, Frank F. J.,Moons, Sam J.,White, Paul B.
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p. 1165 - 1184
(2020/02/22)
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- Site- And enantiodifferentiating C(sp3)-H oxidation enables asymmetric access to structurally and stereochemically diverse saturated cyclic ethers
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A manganese-catalyzed site- and enantiodifferentiating oxidation of C(sp3)-H bonds in saturated cyclic ethers has been described. The mild and practical method is applicable to a range of tetrahydrofurans, tetrahydropyrans, and medium-sized cyclic ethers with multiple stereocenters and diverse substituent patterns in high efficiency with extremely efficient site- and enantiodiscrimination. Late-stage application in complex biological active molecules was further demonstrated. Mechanistic studies by combined experiments and computations elucidated the reaction mechanism and origins of stereoselectivity. The ability to employ ether substrates as the limiting reagent, together with a broad substrate scope, and a high level of chiral recognition, represent a valuable demonstration of the utility of asymmetric C(sp3)-H oxidation in complex molecule synthesis.
- Liu, Lei,Sun, Shutao,Yang, Yiying,Zhang, Dongju,Zhao, Ran
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supporting information
p. 19346 - 19353
(2020/12/01)
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- COMPOUNDS AND THEIR METHODS OF USE
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The present invention is directed to, in part, fused heteroaryl compounds and compositions useful for preventing and/or treating a disease or condition relating to aberrant function of a voltage-gated, sodium ion channel, for example, abnormal late/persistent sodium current. Methods of treating a disease or condition relating to aberrant function of a sodium ion channel including Dravet syndrome or epilepsy are also provided herein.
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Page/Page column 149
(2018/09/08)
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- Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective α-C(sp3)-H Acetalization
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C(sp3)-H bond functionalization has emerged as a robust tool enabling rapid construction of molecular complexity from simple building blocks, and the development of asymmetric versions of this reaction creates a powerful methodology to access enantiopure sp3-rich materials. Herein, we report the stereoselective functionalization of C(sp3)-H bonds of cyclic ethers employing a photochemically active diaryliodonium salt in combination with an anionic phase-transfer catalyst. The synthetic strategy outlined herein allows for regio- and stereochemical control in the α-C-H acetalization of furans and pyrans using alcohol nucleophiles, thus providing the ability to control the configuration at the stereogenic exocyclic acetal carbon.
- Ye, Baihua,Zhao, Jie,Zhao, Ke,McKenna, Jeffrey M.,Toste, F. Dean
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supporting information
p. 8350 - 8356
(2018/07/14)
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- Anti-Selective Catalytic Asymmetric Nitroaldol Reaction of α-Keto Esters: Intriguing Solvent Effect, Flow Reaction, and Synthesis of Active Pharmaceutical Ingredients
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A rare-earth metal/alkali metal bimetallic catalyst proved particularly effective for enantioselectively coupling nitroalkanes and α-keto esters in an anti-selective manner to afford synthetically versatile, densely functionalized, and optically active α-nitro tertiary alcohols. A chiral diamide ligand captured two distinct metal cations, giving rise to a catalytically competent solid-phase heterobimetallic catalyst by simple mixing via self-assembly. The advantage of the solid-phase asymmetric catalyst was realized by successful application to the enantio- and diastereoselective reaction in a continuous-flow platform. The use of closely related solvents in terms of structures and polarity parameters, THF and its methylated congener 2-Me-THF, had an unexpectedly large solvent effect both on the reaction rate and the stereoselectivity. The nitroaldol products share a privileged unit for active pharmaceutical ingredients, as demonstrated by the streamlined enantioselective synthesis of the marketed antifungal agents efinaconazole and albaconazole.
- Karasawa, Tomoya,Oriez, Rapha?l,Kumagai, Naoya,Shibasaki, Masakatsu
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p. 12290 - 12295
(2018/09/27)
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- Selective Hydrogenation of Carboxylic Acids to Alcohols or Alkanes Employing a Heterogeneous Catalyst
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The chemoselective hydrogenation of carboxylic acids to either alcohols or alkanes is reported, employing a heterogeneous bimetallic catalyst consisting of rhenium and palladium supported on graphite. α-Chiral carboxylic acids were hydrogenated without loss of optical purity. The catalyst displays a reverse order of reactivity upon hydrogenation of different carboxylic functions with esters being less reactive than amides and carboxylic acids. This allows for chemoselective hydrogenation of an acid in the presence of an ester or an amide function.
- Ullrich, Johannes,Breit, Bernhard
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p. 785 - 789
(2018/02/14)
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- NOVEL DIHYDROPYRIDINONE AND DIHYDROPYRIMIDINONE COMPOUNDS AND THEIR USE
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The present invention is directed to novel compounds of Formula I; pharmaceutically acceptable salts or solvates thereof, and their use.
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Page/Page column 48; 49
(2017/12/27)
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- 2-OXO-3,4-DIHYDROPYRIDINE-5-CARBOXYLATES AND THEIR USE
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The present invention is directed to novel compounds of Formula (I), pharmaceutically acceptable salts or solvates thereof, and their use.
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Page/Page column 184
(2016/04/20)
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- Substituted Oxopyridine Derivatives and Use Thereof in the Treatment of Cardiovascular Disorders
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The invention relates to substituted oxopyridine derivatives and to processes for their preparation, and also to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular cardiovascular disorders, preferably thrombotic or thromboembolic disorders, and oedemas, and also ophthalmic disorders.
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Paragraph 1264-1265
(2016/05/02)
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- SUBSTITUTED OXOPYRIDINE DERIVATIVES AND USE THEREOF IN THE TREATMENT OF CARDIOVASCULAR DISORDERS
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The invention relates to substituted oxopyridine derivatives and to processes for their preparation, and also to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular cardiovascular disorders, preferably thrombotic or thromboembolic disorders, and oedemas, and also ophthalmic disorders.
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Paragraph 1822-1825
(2016/10/07)
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- FACTOR XIa INHIBITORS
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The present invention provides a compound of Formula (I) and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses, embolisms, hypercoagulability or fibrotic changes. The compounds are selective Factor XIa inhibitors or dual inhibitors of Factor XIa and plasma kallikrein.
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Page/Page column 66; 67
(2015/12/09)
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- SUBSTITUTED TRIAZOLES AND THEIR USE FOR TREATMENT AND/OR PREVENTION NEUROLOGICAL AND PSYCHIATRIC DISORDERS
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This invention relates to compounds of formula (I), their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. A, B, Ar, R1, R2, R3 have meanings given in the description.
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Page/Page column 59
(2013/07/31)
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- NOVEL COMPOUNDS
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This invention relates to compounds of formula I their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. A, B, Ar, R1, R2, R3 have meanings given in the description.
- -
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Paragraph 0310; 0311
(2013/07/25)
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- Libraries of bisdiazaphospholanes and optimization of rhodium-catalyzed enantioselective hydroformylation
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Twelve chiral bis-3,4-diazaphospholane ligands and six alkene substrates (styrene, vinyl acetate, allyloxy-tert-butyldimethylsilane, (E)-1-phenyl-1,3- butadiene, 2,3-dihydrofuran, and 2,5-dihydrofuran) probe the influence of steric bulk on the activity and selectivity of asymmetric hydroformylation (AHF) catalysts. Reaction of an enantiopure bisdiazaphospholane tetraacyl fluoride with primary or secondary amines yields a small library of tetracarboxamides. For all six substrates, manipulation of reaction conditions and bisdiazaphospholane ligands enables state-of-the-art performance (90% or higher ee, good regioselectivity, and high turnover rates). For the nondihydrofuran substrates, the previously reported ligand, (S,S)-2, is generally most effective. However, optimal regio- and enantioselective hydroformylation of 2,3-dihydrofuran (up to 3.8:1 α-isomer/β-isomer ratio and 90% ee for the α-isomer) and 2,5-dihydrofuran (up to 1:30 α-isomer/β- isomer ratio and 95% ee for the β-isomer) arises from bisdiazaphospholanes containing tertiary carboxamides. Hydroformylation of either 2,3- or 2,5-dihydrofuran yields some of the β-formyl product. However, the absolute sense of stereochemistry is inverted. A stereoelectronic map rationalizes the opposing enantiopreferences
- Adint, Tyler T.,Wong, Gene W.,Landis, Clark R.
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p. 4231 - 4238
(2013/06/05)
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- INDOLE DERIVATIVE
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The present invention provides an indole derivative having a melanin-concentrating hormone receptor antagonistic action, which is useful as an agent for the prophylaxis or treatment of obesity and the like. The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof.
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- QUINOLINE DERIVATIVE
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The present invention provides a compound having a melanin-concentrating hormone receptor antagonistic action and low toxicity, which is useful as an agent for the prophylaxis or treatment of obesity and the like. The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof.
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- Zirconium(IV)- and hafnium(IV)-catalyzed highly enantioselective epoxidation of homoallylic and bishomoallylic alcohols
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In this report, zirconium(IV)- and hafnium(IV)-bishydroxamic acid complexes were utilized in the highly enantioselective epoxidation of homoallylic alcohols and bishomoallylic alcohols, which used to be quite difficult substrates for other types of asymmetric epoxidation reactions. The performance of the catalyst was improved by adding polar additive and molecular sieves. For homoallylic alcohols, the reaction could provide epoxy alcohols in up to 83% yield and up to 98% ee, while, for bishomoallylic alcohols, up to 79% yield and 99% ee of epoxy alcohols rather than cyclized tetrahydrofuran compounds could be obtained in most cases.
- Li, Zhi,Yamamoto, Hisashi
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scheme or table
p. 7878 - 7880
(2010/08/04)
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- Regioselective and stereoselective cyclizations of chloropolyols in water: Rapid synthesis of hydroxytetrahydrofurans
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A concise, stereoselective synthesis of functionalized tetrahydrofuranols has been developed that involves heating readily available chloropolyols in water. These reactions are operationally straightforward and chemoselective for the formation of tetrahydrofurans, obviating the need for complicated protecting group strategies. The efficiency of this process is demonstrated in a short asymmetric synthesis of the natural product (+)-goniothalesdiol.
- Kang, Baldip,Chang, Stanley,Decker, Shannon,Britton, Robert
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supporting information; experimental part
p. 1716 - 1719
(2010/09/05)
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- Synthesis of a variety of optically active hydroxylated heterocyclic compounds using epoxide hydrolase technology
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Novel epoxide hydrolases in Yarrowia lipolytica have been shown to hydrolyse a variety of functionalised epoxides with good to excellent stereoselectivity and at high volumetric productivities. Individual biotransformation products have been converted into optically active (R)-(tetrahydrofuran-2-yl)methanol (6), (S)-N-benzyl-3-hydroxypyrrolidine (7), (S)-3-hydroxytetrahydrothiophene (8), (S)-N-benzyl-3-acetoxypiperidine (10), (S)-3-hydroxytetrahydrofuran (16) and (R)-[(S)-N-benzylpyrrolidin-2-yl](phenyl)methanol (20).
- Pienaar, Daniel P.,Mitra, Robin K.,Deventer, Thomas I. van,Botes, Adriana L.
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scheme or table
p. 6752 - 6755
(2009/04/06)
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- 4-AMINO-BENZAMIDE DERIVATIVES AS 5-HT4 RECEPTOR AGONISTS FOR THE TREATMENT OF GASTROINTESTINAL, NEUROLOGICAL AND CARDIOVASCULAR DISORDERS
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The present invention relates to novel benzamide derivatives of formula (I) having pharmacological activity, to processes for their preparation, to compositions containing them and to their use in the treatment of diseases treatable by 5-HT4 agonism.
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Page/Page column 22-23
(2010/11/28)
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- 3-CYCLOALKYLCARBONYL INDOLES AS CANNABINOID RECEPTOR LIGANDS
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The present invention provides novel compounds of Formula (I), which are CB2 selective ligands useful for the treatment of pain.
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Page/Page column 96
(2008/06/13)
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- Substituted-cycloalkyl and oxygenated-cycloalkyl glucokinase activators
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2,3-Di-substituted N-heteroaromatic propionamides with said substitution at the 2-position being a substituted phenyl group and at the 3-position being a polar ring, said propionamides being glucokinase activators which increase insulin secretion in the treatment of type II diabetes.
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- Enzyme-triggered enantioconvergent transformation of haloalkyl epoxides
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Biocatalytic hydrolysis of 2,3-disubstituted rac-cis- and rac-trans-haloalkyl epoxides 1a-8a using the epoxide hydrolase activity of whole bacterial cells furnished the corresponding vicinal diols 1b-8b as intermediates; these (spontaneously) underwent ring closure to yield cyclic products 1c-6c through an enzyme-triggered cascade reaction. In particular, cis-configured substrates (1a, 3a, 5a, 7a) were transformed in an enantioconvergent fashion, which resulted in the formation of single stereoisomeric products in 100% des and up to 92% ees from the racemates.
- Mayer, Sandra F.,Steinreiber, Andreas,Orru, Romano V. A.,Faber, Kurt
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p. 4537 - 4542
(2007/10/03)
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- An enzyme-triggered enantio-convergent cascade-reaction
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The biocatalytic hydrolysis of the (±)-2,3-disubstituted cis-chloroalkyl epoxides 1a and 2a using resting cells of Rhodococcus sp. did not give the corresponding chloroalkyl vic-diols 1b, and 2b, respectively, but furnished the rearranged products (2R,3R)-1c and (2R,3R)-2c in high e.e. as the sole products via an enzyme-triggered enantio-convergent cascade-reaction.
- Mayer, Sandra F.,Steinreiber, Andreas,Orru, Romano V.A.,Faber, Kurt
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- On the selectivity of oxynitrilases towards α-oxygenated aldehydes
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Different α-alkoxy and α,β-di-alkoxy substituted aldehydes have been submitted to the catalytic action of the oxynitrilases from almond (PaHNL) or from Hevea brasiliensis (HbHNL), in order to explore the possibility of using these enzymes for the preparation of complex cyanohydrins. The selectivity of both enzymes towards these compounds was found to be largely dependent on the substitutents, being low with the aldehydes carrying the sterically more demanding phenyl substituent. Contrary to the chemical addition of HCN, which always occurs with a slight preference for the formation of the anti diastereoisomers, the enzymatic cyanuration - occurring with a facial preference, Si or Re according to the biocatalyst used - gave a mixture of cyanohydrins that, depending on the starting enantiomeric aldehyde, can be enriched in the syn diastereoisomers.
- Bianchi, Paola,Roda, Gabriella,Riva, Sergio,Danieli, Bruno,Zabelinskaja-Mackova, Antonina,Griengl, Herfried
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p. 2213 - 2220
(2007/10/03)
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- Chiral recognition of alcohols in the crystal lattice of simple metal complexes of O,O'-dibenzoyltartaric acid: Enantiocomplementarity and simultaneous resolution
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A simple preparative method for the enantiomeric enrichment of alcohols is reported. Crystallization of the complexes of alcohols formed with calcium and zinc O,O'-dibenzoyltartrates led to effective resolutions of the alcohols. However, zinc and calcium dibenzoyltartrates are complementary resolving agents upon coordinative resolution of less-hindered alkoxy alcohols. Mixed copper(II) salts of O,O'-dibenzoyltartaric acid formed with carboxylic acids can also be applied to the resolution of alkoxy alcohols, thereby providing the simultaneous resolution of an alcohol and a carboxylic acid. Zinc dibenzoyltartrate can form coordination compounds with alkoxy alcohols as well as lattice inclusion compounds with simple alcohols as revealed by the four X-ray structures reported here.
- Mravik, Andras,Boecskei, Zsolt,Simon, Kalman,Elekes, Ferenc,Izsaki, Zoltan
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p. 1621 - 1627
(2007/10/03)
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- Synthesis, Structure, and Pharmacological Evaluation of the Stereoisomers of Furnidipine
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The synthesis and pharmacological activities of the four stereoisomers of methyl tetrahydrofuran-2-ylmethyl 2,6-dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (furnidipine) are reported.The four isomers were synthesized by a modified Hantzsch synthesis by reaction of (-)- or (+)-tetrahydrofuran-2-ylmethyl 3-aminocrotonate and methyl 2-acetoacetate or, alternatively, by reaction of (-)- or (+)-tetrahydrofuran-2-ylmethyl 2-acetoacetate and methyl 3-aminocrotonate.The 1:1 diasteromeric mixture thus obtained were separated by chromatography, using poly(D-phenylglycine) as the chiral stationary phase.The enantiomeric purity of the stereoisomers was determined by high-performance liquid chromatography-chiral stationary phase technique (HPLC-CSP).Attempts to obtain crystals of a single stereoisomer failed in different solvent, while methanol crystallization of the product obtained from (+/-)-tetrahydrofuran-2-ylmethyl 2-acetoacetate and methyl 3-aminocrotonate yielded good-quality crystals of the most insoluble racemate which proved to be a mixture of the (SS)/(RR) enantiomers by X-ray crystaloography.Conformational analysis of the stereoisomers, assuming rotation of the aryl substituent and ester groups, shows small energy differences (about 4 kcal*mol-1) between the most and the least favorable conformations.Binding studies were performed using isradipine as a reference ligand.The results showed stereospecificity of the furnidipine isomers in brain, ileum, and cardiac tissues, the (SS) and (SR)-isomers clearly being more potent than their (RR)- and (RS)-enantiomers.The (SS)- and (SR)-isomers were also more selective on cerebral tissue when compared with ileal and cardiac preparations.
- Alajarin, Ramon,Vaguero, Juan J.,Alvarez-Builla, Julio,Pastor, Manuel,Sunkel, Carlos,et al.
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p. 2830 - 2841
(2007/10/02)
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- Synthesis and Chromatographic Separation of the Stereoisomers of Furnidipine
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The four stereoisomers of methyl tetrahydrofuran-2-ylmethyl 2,6-dimethyl-4-(o-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (furnidipine), have been synthesized and separated by chiral chromatography using D-phenylglycine as chiral stationary phase.Enantiomeric purity of stereoisomers is determined by HPLC-CSP technique and configurations deduced via X-ray crystallography.
- Alajarin, Ramon,Alvarez-Builla, Julio,Vaguero, Juan J.,Sunkel, Carlos,Casa-Juana, Miguel Fau de,et al.
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p. 617 - 620
(2007/10/02)
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- How do the gauche and anomeric effects drive the pseudorotational equilibrium of the pentofuranose moiety of nucleosides?
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The conformational characteristics of abasic 1-deoxy sugars 1, 2, and 3 and pentofuranose moieties in 2′,3′-dideoxy-[ddA (6), ddG (7), ddC (8)], 2′-deoxy-[dA (9), dG (10), dC (11)], and ribo-β-D-nucleosides [Ade (12), Gua (13), Cyt (14)] were established through the analysis of vicinal proton-proton coupling constants extracted from their 500-MHz 1H-NMR spectra recorded at 20 K intervals in the temperature range from 278 to 358 K in D2O solution. Two novel deuterated analogues of (S)-tetrahydrofurfuryl alcohol (1), 2-(S)-(hydroxymethyl)-4-(R)-deuteriotetrahydrofuran (4) and 2-(S)-(hydroxymethyl)-3-(S)-deuteriotetrahydrofuran (5), have enabled unequivocal assignment of the complex nine-spin system in its 1H-NMR spectrum. The van't Hoff plots of (ln(XS/XN)] as a function of 1/T gave ΔH° and ΔS° values of pseudorotational equilibrium in pentofuranoses 1-3 and pentofuranose moieties in nucleosides 6-14. The values of ΔH° were dissected into various stereoelectronic effects (gauche versus anomeric effects) of exocyclic substituents on the pentofuranose moiety. Clearly, the gauche effect of the O4′-C4′-C3′-O3′ fragment drives the pseudorotational equilibrium to the S-type conformations, while the gauche effect of the O4′-C1′-C2′-O2′ fragment pushes the pseudorotational equilibrium to the N. These gauche effects are the strongest factors responsible for driving the N ? S pseudorotational equilibrium. The strength of the gauche effect of the O4′-C4′-C3′-O3′ fragment in abasic sugars 1-3 is further tuned by the presence of a heterocyclic base at C1′ in nucleosides 6-14. The relatively weaker anomeric effect of the heterocyclic base drives the N ? S equilibrium to the N. The assessment of the relative strengths of the anomeric effects in 2′,3′-dideoxy, 2′-deoxy-, and ribo-β-D-nucleosides has shown that the anomeric effect of the cytosine base is stronger than the anomeric effect of the adenine or guanine base. The experimental data suggest that the anomeric effect is considerably reduced as O4′ experiences the electron-withdrawing effect(s) of 2′(3′)-hydroxyls. The differences in the conformational preferences found in purine and pyrimidine ribonucleosides were additionally attributed to the distinct relative strength of the gauche effect of the N-C1′-C2′-O2′ fragment. The preference for the gauche orientation of the N-C1′-C2′-O2′ fragment and therefore S-type sugar conformation is affected by the nature of the purine or pyrimidine glycosyl nitrogen atom.
- Plavec, Janez,Tong, Weimin,Chattopadhyaya, Jyoti
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p. 9734 - 9746
(2007/10/02)
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- ABSOLUTE CONFIGURATIONS OF SOME HETEROCYCLIC ACIDS
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Employing the method of asymmetric transformation, the absolute configurations of heterocyclic acids III, IV, Va, and VIIa have been determined.The acids Va and VIIa were chemically correlated with alcohols of known absolute configurations.
- Cervinka, Otakar,Bajanzulyn, Ojuuncimeg,Fabryova, Anna,Sackus, Algirdas
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p. 404 - 407
(2007/10/02)
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