Novel P,N-bidentate phosphite ligands in asymmetric catalysis.

Abstract:

:Results achieved by the authors in the synthesis of chiral P,N-phosphite ligands are summarized. Three groups of new chiral P,N-phosphites are discussed, namely, ligands derived from 1,1'-bi-2-naphthol, ligands possessing an acyclic phosphorus center, and P*-chiral ligands derived from (S)-2-anilinomethylpyrrolidine. An overview of complexation of the ligands with Rh(I) and Pd(II) precursors is given. Accessibility and stability of chiral phosphite ligands possessing acyclic phosphorus was analyzed for the first time along with their efficiency in terms of stereoselectivity. The title ligands are shown to be highly efficient in the Pd-catalyzed allylic alkylation (up to 85% ee) and, especially, allylic sulfonylation (up to 97% ee) reactions in certain cases outperformed all known catalytic systems.

journal_name

Chirality

journal_title

Chirality

authors

Gavrilov KN,Bondarev OG,Korostylev AV,Polosukhin AI,Tsarev VN,Kadilnikov NE,Lyubimov SE,Shiryaev AA,Zheglov SV,Gais HJ,Davankov VA

doi

10.1002/chir.10258

subject

Has Abstract

pub_date

2003-01-01 00:00:00

pages

S97-S103

eissn

0899-0042

issn

1520-636X

journal_volume

15 Suppl

pub_type

杂志文章
  • Synthesis and stereochemistry of dispiro substituted pyridazines: application of ellipticity-absorbance ratio spectra for proving enantiomeric relationship by HPLC-CD/UV detection.

    abstract::The aim of our study was to synthesize vinylic and pyrido-fused pyridazines with a spirano moiety and to investigate their stereochemistry by spectroscopic and HPLC analyses. The vinylic compounds 5 were obtained by Knoevenagel condensation of cyclohexylidene malonates 1 with pyridazinecarbaldehyde 2. Compound 5b exhi...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10096

    authors: Beke G,Gergely A,Szász G,Szentesi A,Nyitray J,Barabás O,Harmath V,Mátyus P

    更新日期:2002-05-15 00:00:00

  • Stereoselective pharmacokinetics and metabolism of flobufen in guinea pigs.

    abstract::Stereoselective aspects of pharmacokinetics and metabolism of a chiral nonsteroidal antiinflammatory drug, flobufen, 4-(2', 4'-difluorobiphenyl-4-yl)-2-methyl-4-oxobutanoic acid, were studied in male guinea pigs after p.o. administration of racemic flobufen (rac-flobufen) at a dose of 10 mg/kg. Blood samples were coll...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10288

    authors: Trejtnar F,Král R,Pávek P,Wsól V

    更新日期:2003-10-01 00:00:00

  • Chiral aggregates and asymmetric induction of the reduction of prochiral ketones.

    abstract::The aim of this work was to establish structure-reactivity relationships between chiral aggregates (micelles, vesicles, and "pseudo-micelles" of amphiphilic dendrimers) and asymmetric induction. In water, micelles or vesicles formed with sugar-headed surfactants gave less than 10% ee in the reduction of prochiral keto...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/1520-636X(2001)13:1<24::AID-CHIR5>3.0.CO;2

    authors: Rico-Lattes I I,Schmitzer A,Perez E,Lattes A

    更新日期:2001-01-01 00:00:00

  • Structure and unexpected chiroptical properties of chiral 4-pyrrolidinyl substituted 2(5H)-furanones.

    abstract::Planar 2(5H)-furanones substituted at C4 with a chiral pyrrolidinyl group show CD spectra which are apparently due to the distortion of the C4-N1 bond of sp2 character from the plane defined by the 2(5H)-furanone ring atoms and/or due to the presence of substituents in the pyrrolidine ring. This is a new, previously n...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20059

    authors: Gawroński J,Gawrońska K,Kwit M,Kacprzak K,Rychlewska U

    更新日期:2004-08-01 00:00:00

  • Secondary phosphine oxides: tautomerism and chiral recognition monitored by multinuclear NMR spectroscopy of their Rh2[(R)-MTPA]4 adducts.

    abstract::Six secondary phosphine oxides and their tautomeric equilibria as free ligands and in the presence of an equimolar amount of the chiral dirhodium complex Rh* are described and discussed. Discrimination of enantiomers is easily possible by inspecting the (31)P NMR resonances; some (1)H and (13)C NMR resonances are usef...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10306

    authors: Magiera D,Szmigielska A,Pietrusiewicz KM,Duddeck H

    更新日期:2004-01-01 00:00:00

  • Chirality as an inherent general property of matter.

    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

    authors: Davankov V

    更新日期:2006-08-01 00:00:00

  • Theoretical study of N-heterocyclic carbenes-catalyzed cascade annulation of benzodienones and enals.

    abstract::Growing attention in developing new N-heterocyclic carbene (NHC)-mediated reactions involving homoenolate intermediates has prompted our interest in exploring the mechanistic details of the related reactions. In this work, we carried out a detailed theoretical study for the NHC-catalyzed annulation reaction of cinnama...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22157

    authors: Sun H,Fang X,Chi YR,Li G

    更新日期:2013-09-01 00:00:00

  • Spectroscopic studies on nicotine and nornicotine in the UV region.

    abstract::The UV absorption and electronic circular dichroism (ECD) spectra of (R)- and (S)-nicotine and (S)-nornicotine in aqueous solution were measured to a significantly lower wavelength range than previously reported, allowing the identification of four previously unobserved electronic transitions. The ECD spectra of the t...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22141

    authors: Clayton PM,Vas CA,Bui TT,Drake AF,McAdam K

    更新日期:2013-05-01 00:00:00

  • The possible role of enantiodiscrimination in bilirubin toxicity.

    abstract::The possibility that enantiodiscrimination of bilirubin might be involved in neuronal membrane destabilization, and therefore in bilirubin toxicity, was investigated, by circular dichroism, on model membranes composed of phospholipids. The equilibrium between bilirubin enantiomers is displaced at some extent by the in...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20610

    authors: Bernardini C,D'Arrigo P,Elemento G,Mancini G,Servi S,Sorrenti A

    更新日期:2009-01-01 00:00:00

  • Pimarane diterpenes: Natural source, stereochemical configuration, and biological activity.

    abstract::Plants and fungi are seemingly inexhaustible sources of interesting natural products with remarkable structural and biological diversity. One of the most important groups is the terpenes, ubiquitous natural products that are generated by 2 now well-established biosynthetic pathways: the older mevalonate and the more r...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.23009

    authors: Reveglia P,Cimmino A,Masi M,Nocera P,Berova N,Ellestad G,Evidente A

    更新日期:2018-10-01 00:00:00

  • Stereoselective chiral inversion of pantoprazole enantiomers after separate doses to rats.

    abstract::(+/-)-Pantoprazole ((+/-)-PAN), (+/-)-5-(difluoromethoxy)-2-[[3.4-dimethoxy-2-pyridinyl)methyl]sul finyl]- 1H-benzimidazole) is a chiral sulfoxide that is used clinically as a racemic mixture. The disposition kinetics of (+)-PAN and (-)-PAN given separately has been studied in rats. Serum levels of (+)- and (-)-PAN an...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1998)10:8<747::AID-CHIR5>3

    authors: Masubuchi N,Yamazaki H,Tanaka M

    更新日期:1998-01-01 00:00:00

  • Asymmetric allylation of α-ketoester-derived N-benzoylhydrazones promoted by chiral sulfoxides/N-oxides Lewis bases: highly enantioselective synthesis of quaternary α-substituted α-allyl-α-amino acids.

    abstract::Chiral sulfoxides/N-oxides (R)-1 and (R,R)-2 are effective chiral promoters in the enantioselective allylation of α-keto ester N-benzoylhydrazone derivatives 3a-g to generate the corresponding N-benzoylhydrazine derivatives 4a-g, with enantiomeric excesses as high as 98%. Representative hydrazine derivatives 4a-b were...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22159

    authors: Reyes-Rangel G,Bandala Y,García-Flores F,Juaristi E

    更新日期:2013-09-01 00:00:00

  • Separation and determination of tetracycline hydrochloride in real water samples using binary small molecule alcohol-salt aqueous two-phase system coupled with high-performance liquid chromatography.

    abstract::An environmental and sensitive sample pretreatment method was established and combined with high-performance liquid chromatography (HPLC) for the analysis of tetracycline hydrochloride (TC) in feed water and lake water. One element small molecule alcohol-salt aqueous two-phase system (ATPS) cannot effectively adjust t...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23080

    authors: Guo DG,Ni L,Wang L,Shao L

    更新日期:2019-09-01 00:00:00

  • Influence of endotoxin on the stereoselective pharmacokinetics of oxprenolol, propranolol, and verapamil in the rat.

    abstract::The influence of endotoxin-induced inflammation on the enantioselective pharmacokinetics of propranolol, oxprenolol, and verapamil, which bind to alpha 1-acid glycoprotein, was studied in the rat. The racemic mixtures were given orally. In the control animals, for propranolol and oxprenolol, the plasma concentrations ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530060508

    authors: Laethem ME,Belpaire FM,Wijnant P,Rosseel MT,Bogaert MG

    更新日期:1994-01-01 00:00:00

  • Enantioselectivity in the metabolism of mexiletine by conjugation in female patients with the arrhythmic form of chronic Chagas' heart disease.

    abstract::The phenomenon of enantioselectivity in the metabolism of mexiletine (MEX) conjugation was investigated in eight female patients with the arrhythmic form of chronic Chagas' heart disease treated with racemic mexiletine hydrochloride (two 100 mg capsules every 8 hr). Blood samples were collected up to 24 hr after the a...

    journal_title:Chirality

    pub_type: 临床试验,杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:1<29::AID-CHIR5>3.

    authors: Lanchote VL,Cesarino EJ,Santos VJ,Mere Júnior Y,Santos SR

    更新日期:1999-01-01 00:00:00

  • Dynorphin A analogs containing a conformationally constrained phenylalanine derivative in position 4: reversal of preferred stereochemistry for opioid receptor affinity and discrimination of kappa vs. delta receptors.

    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.

    authors: Aldrich JV,Zheng QI,Murray TF

    更新日期:2001-01-01 00:00:00

  • Evaluation of the enantioselectivity of capillary electrokinetic chromatography using ethanediamine-bonded poly (glycidyl methacrylate) microspheres as the pseudostationary phases.

    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

    authors: Sun X,Yu T,Xu G,Du Y,Chen J,Li X

    更新日期:2019-02-01 00:00:00

  • Gas chromatographic separation of saturated aliphatic hydrocarbon enantiomers on permethylated beta-cyclodextrin.

    abstract::Enantiomers of chiral aliphatic hydrocarbons are generally difficult to separate because they lack functional groups to be derivatized in order to generate diastereomers. The systematic and quantitative separation of a series of branched hydrocarbon enantiomers using a chiral cyclodextrin stationary phase and a cryost...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10269

    authors: Meierhenrich UJ,Nguyen MJ,Barbier B,Brack A,Thiemann WH

    更新日期:2003-01-01 00:00:00

  • Channel-like crystal structure of cinchoninium L-O-phosphoserine salt dihydrate.

    abstract::Studies on the interactions between L-O- phosphoserine, as one of the simplest fragments of membrane components, and the Cinchona alkaloid cinchonine, in the crystalline state were performed. Cinchoninium L-O-phosposerine salt dihydrate (PhSerCin) crystallizes in a monoclinic crystal system, space group P2(1), with un...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20784

    authors: Wesełucha-Birczyńska A,Oleksyn BJ,Watroba J

    更新日期:2010-06-01 00:00:00

  • Enantiomeric separation and determination of absolute stereochemistry of asymmetric molecules in drug discovery: building chiral technology toolboxes.

    abstract::The application of Chiral Technology, or the (extensive) use of techniques or tools for the determination of absolute stereochemistry and the enantiomeric or chiral separation of racemic small molecule potential lead compounds, has been critical to successfully discovering and developing chiral drugs in the pharmaceut...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.20399

    authors: McConnell O,Bach A 2nd,Balibar C,Byrne N,Cai Y,Carter G,Chlenov M,Di L,Fan K,Goljer I,He Y,Herold D,Kagan M,Kerns E,Koehn F,Kraml C,Marathias V,Marquez B,McDonald L,Nogle L,Petucci C,Schlingmann G,Tawa G,Tis

    更新日期:2007-09-01 00:00:00

  • Chiral discrimination by albumin: a mechanistic study of liquid chromatographic optical resolution of nonaromatic carboxylic acids.

    abstract::In order to get further insight into the mechanism by which bovine serum albumin (BSA) discriminates between enantiomers of organic acids, some radioisotopically labeled, nonaromatic carboxylic acids were studied under varying mobile phase conditions. It was found for a series of N-alkanoyl-DL-[3H]leucines that the D-...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530050503

    authors: Allenmark S

    更新日期:1993-01-01 00:00:00

  • Conformational and Chiral Properties of Cyclic-tri(N-methyl-meta-benzamide) Bearing Amidino Groups.

    abstract::Cyclic triamides bearing amidino groups at the meta position of the phenyl rings were synthesized, and their conformational properties in the crystal and in solution were examined. Compound exists as a capsule-type dimer of the enantiomers with a bowl-shaped syn conformation in the crystal state. Compound exists mainl...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22476

    authors: Nishiyama S,Urushibara K,Masu H,Azumaya I,Kagechika H,Tanatani A

    更新日期:2015-08-01 00:00:00

  • Modulatory effect of chiral nonsteroidal anti-inflammatory drugs on apoptosis of human neutrophils.

    abstract::Polymorphonuclear neutrophils (PMNs) are short-lived leukocytes that die by apoptosis. Although PMNs are crucial in the defense against infection, they have been implicated in the pathogenesis of tissue injury observed in inflammatory diseases. The induction or prevention of PMN apoptosis is currently discussed as a k...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20516

    authors: Zielińska-Przyjemska M,Główka FK,Klaczyńska J

    更新日期:2008-02-01 00:00:00

  • Resolution of enantiomers of novel C2 -symmetric aminobisphosphinic acids via diastereomeric salt formation with quinine.

    abstract::C2 -symmetric N,N-bis(phosphinomethyl)amines were prepared by the thermal reaction of aromatic aldehydes with ammonia and hypophosphorus acid as previously described. Both enantiomers of C2 -symmetric N,N-bis(phosphinomethyl)amine were obtained in a high enantiomeric purity through the diastereomeric salt formation wi...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22391

    authors: Kaboudin B,Faghihi MR,Kazemi F,Yokomatsu T

    更新日期:2015-01-01 00:00:00

  • N,N-dimethylcarbamyl derivatives of oxazepam.

    abstract::Three N,N-dimethylcarbamyl derivatives of oxazepam (1-(N,N-dimethylcarbamyl)oxazepam, 3-O-(N,N-dimethylcarbamyl)oxazepam, and 1,3-O-bis(N,N-dimethylcarbamyl) oxazepam) and a 3-O-acyl-1-(N,N-dimethylcarbamyl)-oxazepam were synthesized from either oxazepam or demoxepam. Enantiomeric pairs of these derivatives and of cam...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530030313

    authors: Yang SK,Lu XL

    更新日期:1991-01-01 00:00:00

  • Optically active α-phenylethylamine as efficient organocatalyst in the solvent-free reactions between 2,3-butanedione and conjugated nitroolefins.

    abstract::(R)-(+) and (S)-(-)-1-phenylethylamine have been shown to promote highly diastereoselective and complementary enantioselective formal [3 + 2]carbocyclization reactions between 2,3-butanedione and conjugated nitroalkenes with formation of enantiomerically rich 2-hydroxy-3-nitrocyclopentanone derivatives. The reactions ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22088

    authors: Felluga F,Forzato C,Nitti P,Pitacco G,Prati F,Valentin E,Zangrando E

    更新日期:2012-12-01 00:00:00

  • Stereospecific pH-dependent degradation kinetics of R- and S-naproxen-beta-l-O-acyl-glucuronide.

    abstract::The hydrolysis and acyl migration of biosynthetic S-naproxen-beta-l-O-acyl glucuronide (I) and R-naproxen-beta-l-O-acyl glucuronide (II) was followed by HPLC. Nine first-order kinetic rate constants for the hydrolysis and acyl migration between the beta-l-O-acyl glucuronide, its alpha/beta-2, alpha/beta-3-, alpha/beta...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10047

    authors: Mortensen RW,Sidelmann UG,Tjørnelund J,Hansen SH

    更新日期:2002-05-05 00:00:00

  • Enantiomerization and enantioselective bioaccumulation of metalaxyl in Tenebrio molitor larvae.

    abstract::The enantiomerization and enantioselective bioaccumulation of metalaxyl by a single dose of exposure to Tenebrio molitor larvae under laboratory condition were studied by high-performance liquid chromatography tandem mass spectroscopy (HPLC-MS/MS) based on a ChiralcelOD-3R [cellulosetris-tris-(3, 5-dichlorophenyl-carb...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22269

    authors: Gao Y,Wang H,Qin F,Xu P,Lv X,Li J,Guo B

    更新日期:2014-02-01 00:00:00

  • Stereolability of chiral ruthenium catalysts with frozen NHC ligand conformations investigated by dynamic-HPLC.

    abstract::The stereolability of chiral Hoveyda-Grubbs II type ruthenium complexes bearing N-heterocyclic carbene (NHC) ligands with Syn-phenyl groups on the backbone and Syn- or Anti-oriented o-tolyl N-substituents was studied by resorting to dynamic high-performance liquid chromatography (D-HPLC). A complete chromatographic pi...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22487

    authors: Menta S,Pierini M,Cirilli R,Grisi F,Perfetto A,Ciogli A

    更新日期:2015-10-01 00:00:00

  • Solid-state circular dichroism and hydrogen bonding, part 2: the case of hypothemycin re-investigated.

    abstract::The impact of crystalline forces on the solid-state circular dichroism (CD) spectrum of hypothemycin (), a biologically active molecule extracted from natural sources, has been analyzed by means of time-dependent density functional theory CD calculations. Input structures were extracted from the X-ray geometry of and ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22008

    authors: Pescitelli G

    更新日期:2012-09-01 00:00:00