Abstract:
:Anodic oxidation of 1-acetoxy-3,4-dihydronaphthalene (1) and alpha-acetoxy-beta-alkylstyrenes (3) at -78 degrees C in a mixed solvent of acetonitrile (CH(3)CN), tetrahydrofuran (THF), and acetic acid (AcOH) containing (S)-tetraethylammonium camphorsulfonate as a chiral supporting electrolyte brought about enantioselective formation of the corresponding 2-acetoxy-1-tetralones (2) and (R)-2-acetoxy-1-phenyl-1-alkanone (4) with maximum enantiomeric excess (ee) of 44% and 21%, respectively. Introduction of a 7-methoxy group into 1 and increase in bulkiness of a beta-alkyl group in 3 resulted in improvement of enantioselectivity of the reactions.
journal_name
Chiralityjournal_title
Chiralityauthors
Maekawa H,Itoh K,Goda S,Nishiguchi Idoi
10.1002/chir.10165subject
Has Abstractpub_date
2003-01-01 00:00:00pages
95-100issue
1eissn
0899-0042issn
1520-636Xjournal_volume
15pub_type
杂志文章相关文献
CHIRALITY文献大全abstract::Three chiral derivatives of the alkaloid sparteine (bispidines), characterized by the 3,7-diazabicyclo[3.3.1]nonane moiety, were designed as efficient ligands in a number of enantioselective reactions due to their metal coordination properties. A full evaluation of the 3D properties of the compounds was carried out, a...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22586
更新日期:2016-04-01 00:00:00
abstract::Analogs of the opioid peptide [D-Ala8]dynorphin A-(1-11)NH2 containing optically pure (R)- and (S)-2-aminotetralin-2-carboxylic acid (Atc) in position 4 were synthesized and evaluated for opioid receptor affinity. These peptides are the first reported dynorphin A analogs containing a conformationally constrained amino...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/1520-636X(2001)13:3<125::AID-CHIR1008>3.0.
更新日期:2001-01-01 00:00:00
abstract::Achiral 4-isopropyltropolone methyl ether (3) included in an optically active host compound (-)-1 yielded optically active photocyclization products (-)-5 and (-)-6 in 96 and 90% ee, respectively, upon photoirradiation in the solid state. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10091
更新日期:2002-07-01 00:00:00
abstract::Two diastereomeric cationic surfactants derived from L-proline, in which the second chiral center is a quaternary nitrogen, have been separated and fully characterized. The recognition properties of the aggregates formed by the two diastereomeric surfactants have been investigated by circular dichroism and (1)H NMR th...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10230
更新日期:2003-05-15 00:00:00
abstract::This article describes a very useful extension of an unique column switching technique called "Simulated Moving Columns" (SMC) that was previously reported for chiral high performance liquid chromatography (HPLC) (Zhang and McConnell, Journal of Chromatography A 2004;1028:227-238). SMC uses two or three short chiral c...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20409
更新日期:2007-09-01 00:00:00
abstract::Synthetic pyrethroid insecticides are chiral compounds with multiple asymmetric positions. In this study, isomers of four commonly used pyrethroids were separated at the enantiomeric level by enantioselective high-performance liquid chromatography (HPLC), and differences between enantiomers in aquatic toxicity were ch...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20122
更新日期:2005-01-01 00:00:00
abstract::High-performance liquid chromatography (HPLC) is a powerful method in the area of chiral separation. In this study, a method of HPLC using carboxymethyl-β-cyclodextrin (CM-β-CD) as chiral selector was developed for enantioseparation of nine indanone and tetralone derivatives. The separation was performed on a conventi...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22665
更新日期:2017-01-01 00:00:00
abstract::3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid (deoxycholic acid DCA) is able to discriminate between the R- and S-enantiomers of camphorquinone and endo-(+)-3-bromocamphor and select only the S-enantiomers from a racemic mixture. DCA forms novel well ordered 1:1 adducts with (1S)-(+)-camphorquinone and (1S)-endo-(...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20561
更新日期:2008-07-01 00:00:00
abstract::This paper reports the enantioseparation of β-hydroxy-1,2,3-triazole derivatives, which present a broad range of biological properties, by supercritical fluid chromatography (SFC) and high-performance liquid chromatography techniques (HPLC). Polysaccharide-based chiral columns (cellulose and amylose) were used to eval...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22851
更新日期:2018-07-01 00:00:00
abstract::A statement has been formulated that chirality is an indispensable inherent property of all material objects, at one level of organization of matter or another. The translation of chirality from one level of material objects to another deserves our attention. The parity violation of weak interactions can be discussed ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20271
更新日期:2006-08-01 00:00:00
abstract::In this work, a new capillary electrokinetic chromatography (EKC) approach using ethanediamine-bonded poly (glycidyl methacrylate) (Ami-PGMA) microspheres as pseudostationary phases (PSPs) for enantioseparation with a polysaccharide, chondroitin sulfate E (CSE), as the chiral selector. The CSE@Ami-PGMA EKC system was ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23035
更新日期:2019-02-01 00:00:00
abstract::Racemic N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5), a putative postsynaptic agonist and presynaptic antagonist at muscarinic receptors, was resolved into the enantiomers by a new method suitable for large scale preparation. The method involves a chemoselective N-debenzylation as the key step. The en...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.530040607
更新日期:1992-01-01 00:00:00
abstract::A method for the determination of (R)- and (S)-atenolol in human plasma and urine is described. The enantiomers of atenolol are extracted into dichloromethane containing 3% heptafluorobutanol followed by acetylation with acetic anhydride at 60 degrees C for 2 h. The acetylated enantiomers were separated on a chiral al...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.530010306
更新日期:1989-01-01 00:00:00
abstract::Vibrational circular dichroism (VCD) spectra of (+)-alpha-pinene solutions in carbon tetrachloride have been measured in the range of volume fractions 5-100% (v/v) in the mid-infrared region. The concentration dependence measured was statistically analyzed with the aim of obtaining a reliable correlation between the V...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(2000)12:4<199::AID-CHIR6>3
更新日期:2000-05-01 00:00:00
abstract::The size, sign, and profile of induced circular dichroism (CD) features in the Soret region are reliable indicators of the binding modes of porphyrins and metalloporphyrins to DNA. Porphyrins shown (using such CD criteria) to be intercalators in monodispersed DNA duplexes prove extremely useful for the detection and c...
journal_title:Chirality
pub_type: 杂志文章,评审
doi:10.1002/chir.10206
更新日期:2003-05-05 00:00:00
abstract::After alkylation of a fraction of the total alpha-adrenoreceptors by phenoxybenzamine in rat vas deferens, the dissociation constants of (-)- and (+)-epinephrine in functional studies were 7 X 10(-7) M and 2 X 10(-5) M, respectively. In the adrenoreceptor-containing tissue fraction, when 3H-labeled WB4101 was used as ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.530010106
更新日期:1989-01-01 00:00:00
abstract::Although the organocatalytic direct asymmetric Michael reactions of carbonyl compounds to nitroalkenes have been investigated intensely, the Michael reaction of the thioether-based donors remains a rather undeveloped field. This work concerns the asymmetric Michael addition of aryl sulfanyl-propan-2-one to nitroalkene...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20689
更新日期:2010-07-01 00:00:00
abstract::The chiral fungicide furametpyr is widely used in the rice field to control rice sheath blight; however, furametpyr enantiomers are treated as just one compound in traditional achiral analysis, which gives only partial information. An effective chiral analytical method was developed for the resolution and determinatio...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22232
更新日期:2013-12-01 00:00:00
abstract::The adsorption of heptahelicene, a helically shaped polyaromatic hydrocarbon (C(30)H(18)), on a Cu(111) surface was studied by means of thermal desorption mass spectrometry (TDMS) and low energy electron diffraction (LEED) at temperatures between 130-1,000 K under ultrahigh vacuum (UHV) conditions. The molecule in the...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10006
更新日期:2001-01-01 00:00:00
abstract::Isophthalic and terephthalic acid monoesters of cyclic nigerosyl-(1→6)-nigerose (CNN), a cyclic tetrasaccharide composed of four d-glucopyranosyl residues connected by alternating α-1,3- and α-1,6-linkages, were synthesized as novel chiral supramolecular sensitizers for enantiodifferentiating photoisomerization of (Z)...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22014
更新日期:2012-11-01 00:00:00
abstract::SCH 56592 is a novel triazole antifungal agent that is active both orally and intravenously in animal models of infection. This compound is in Phase II-III clinical trials for the treatment of systemic fungal infections. SCH 56592 is a single enantiomer with four stereogenic centers; therefore, it was necessary to eva...
journal_title:Chirality
pub_type: 临床试验,杂志文章
doi:10.1002/1520-636X(2000)12:7<590::AID-CHIR7>3.0.CO;
更新日期:2000-07-01 00:00:00
abstract::The concentration sensitivity of a racemic drug (chlorpheniramine maleate) in chiral capillary electrophoresis with electrospray ionization – mass spectrometric detection was improved ~500-fold via stacking. Enantiomeric separation was achieved through the use of a neutral chiral pseudostationary phase (2-hydroxpropyl...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22257
更新日期:2014-11-01 00:00:00
abstract::Weinreb amide 3 was synthesized using isobutyl chloroformate, carbonyldiimidazole, or ethylcarbodiimide as the coupling agent in the reaction of Boc-phenylalanine with O,N-dimethylhydroxylamine hydrochloride. An optically active oil was isolated along with an optically inactive solid irrespective of the type of coupli...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(2000)12:1<2::AID-CHIR2>3.0
更新日期:2000-01-01 00:00:00
abstract::The opening of ortho-substituted phenyl oxiranes by borohydrides is described both in aqueous and solid phases. Some remarkable differences in the regioselectivity and inversion of enantioselectivity of oxirane ring-opening are reported. The results obtained are compared with previous studies and have allowed some fac...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1999)11:7<541::AID-CHIR5>3
更新日期:1999-01-01 00:00:00
abstract::C(25) highly branched isoprenoid (HBI) alkenes are ubiquitous lipids found in geochemical samples around the globe. The origins of these widespread geochemicals are believed to be restricted to a limited number of diatoms, including Haslea ostrearia (and related species), Rhizosolenia setigera, and Pleurosigma interme...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.1053
更新日期:2001-08-01 00:00:00
abstract::Compound A, a novel disubstituted pyrrolidine acid, is a member of a new class of agents that are potentially useful for the treatment of diabetes and dyslipidemia. The absolute configuration of this compound was determined by using vibrational circular dichroism (VCD). The results are in agreement with the assignment...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20316
更新日期:2006-09-01 00:00:00
abstract::Bath salts, fumigations, cleaners and air fresheners, behind these terms substances are hidden, which count as "Legal Highs". These fancy names are used to pretend Legal Highs as harmless compounds, to circumvent legal regulations for marketing as well as to increase the sales. Besides classic illicit drugs of synthet...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23135
更新日期:2020-01-01 00:00:00
abstract::Herein, we present the solution-state NMR studies on dextromethorphan (1) under both isotropic and anisotropic conditions. From the measurement of 22 residual dipolar couplings using a stretched polystyrene gel (PS), we show that accurate and detailed structural information is readily determined including the relative...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20703
更新日期:2010-01-01 00:00:00
abstract::Ibuprofen was used to demonstrate that isolated rat hepatocytes offer a suitable in vitro model to investigate the metabolic chiral inversion of anti-inflammatory 2-arylpropionic acids (profens). The inversion of the pharmacologically inactive (-)-(R)-ibuprofen to the active (+)-(S)-ibuprofen was shown to obey apparen...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.530020203
更新日期:1990-01-01 00:00:00
abstract::Vitamin E is an essential nutrient of still increasing economic importance. Vitamin E derivatives include many nonracemic chiral compounds whose chirooptical characterization is scarcely described in the literature. We report the CD spectra of delta-tocopherol and its unsaturated analog delta-tocotrienol. TDDFT calcul...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20591
更新日期:2009-01-01 00:00:00