Synthesis and characterization of conformationally rigid chiral pyridine-N-heterocyclic carbene-based palladacycles with an unexpected Pd-N bond cleavage.

Abstract:

:The versatility of a previously developed method for the synthesis of chiral carbene-based palladacycles is demonstrated through the synthesis of two new chiral pyridine-functionalized N-heterocyclic carbene palladacycles with different wingtip groups. The efficiency in their resolution with different counter anions and different chiral amino acid salt auxiliaries has been studied. The absolute stereochemistries of all the chiral compounds were confirmed by single crystal X-ray crystallography. An unexpected Pd-N bond cleavage that resulted in the racemization of the α-carbon center in these complexes has also been investigated.

journal_name

Chirality

journal_title

Chirality

authors

Ng KH,Li Y,Tan WX,Chiang M,Pullarkat SA

doi

10.1002/chir.22116

subject

Has Abstract

pub_date

2013-03-01 00:00:00

pages

149-59

issue

3

eissn

0899-0042

issn

1520-636X

journal_volume

25

pub_type

杂志文章
  • Three-Dimensional Chemical Structure Search Using the Conformational Code for Organic Molecules (CCOM) Program.

    abstract::Searching the 3D structural fragments of organic molecules is challenging because of structural differences between X-ray and theoretically calculated geometries and the conformational flexibility of substituents. The codification program called Conformational Code for Organic Molecules (CCOM) can be used to unambiguo...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22596

    authors: Izumi H,Nafie LA,Dukor RK

    更新日期:2016-05-01 00:00:00

  • Evaluation of the enantiomeric composition of amino acids in tobacco.

    abstract::Despite the fact that several studies have reported the concentrations of various free amino acids in tobacco, their enantiomeric composition is unknown. Both the absolute and enantiomeric compositions of proline, alanine, asparagine, aspartic acid, valine, methionine, leucine,and phenylalanine were determined for thr...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:8<669::AID-CHIR10>

    authors: Kullman JP,Chen X,Armstrong DW

    更新日期:1999-01-01 00:00:00

  • Conformational spaces of Cinchona alkaloids.

    abstract::A systematic and comprehensive study of the conformational spaces of the Cinchona alkaloids quinine, quinidine, cinchonine, cinchonidine, epiquinine, epiquinidine, epicinchonine, and epicinchonidine using the semiempirical PM3 method is described. The results were analyzed in terms of syn/anti and open/closed/hindered...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10265

    authors: Caner H,Biedermann PU,Agranat I

    更新日期:2003-08-01 00:00:00

  • Efficient resolution of venlafaxine and mechanism study via X-ray crystallography.

    abstract::Numbers of resolving factors were investigated to improve resolution of venlafaxine 1. An effective resolving agent, O,O'-di-p-toluoyl-(R, R)-tartaric acid 2, was screened using similar method of 'Dutch resolution' from tartaric acid derivatives. The resolution efficiency was up to 88.4%, when the ratio of rac-1 and 2...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22790

    authors: Liu ZJ,Liu H,Chen XW,Lin M,Hu Y,Tuo X,Yuan ZY,Sun XX

    更新日期:2018-03-01 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

  • Absolute configuration of oplopanone derivatives from Serphidium stenocephalum: ECD spectra of acyclic ketones with front-octant contributions.

    abstract::The electronic circular dichroism (ECD) spectra of two sesquiterpenoids (1 and 2) related to oplopanone, obtained from a methanolic extract of the plant Serphidium stenocephalum (Artemisia stenocephala), were measured and reproduced by means of time-dependent density functional theory (TDDFT) calculations, establishin...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22263

    authors: Shafiq N,Saleem M,Riaz N,Tousif MI,Jabbar A,Tareen RB,Pescitelli G

    更新日期:2014-01-01 00:00:00

  • Circular dichroism eigenspectra of polyproline II and β-strand conformers of trialanine in water: Singular value decomposition analysis.

    abstract::Despite that a number of experimental and theoretical investigations have been carried out to determine the structure of trialanine in water, the reported populations of polyproline II (PPII) and β-strand conformers vary and were found to be dependent on which spectroscopic method was used. Such discrepancies are due ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20870

    authors: Oh KI,Lee KK,Park EK,Yoo DG,Hwang GS,Cho M

    更新日期:2010-01-01 00:00:00

  • Chemoenzymatic and microbial dynamic kinetic resolutions.

    abstract::This review tracks a decade of dynamic kinetic resolution developments with a biocatalytic inclination using enzymatic/microbial means for the resolution part followed by the racemization reactions either by means of enzymatic or chemocatalyst. These fast developments are due to the ability of the biocatalysts to sign...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20619

    authors: Kamaruddin AH,Uzir MH,Aboul-Enein HY,Halim HN

    更新日期:2009-04-01 00:00:00

  • Chiral discrimination of the analgesic cizolirtine by using cyclodextrins: A (1)H NMR study on the solution structures of their host-guest complexes.

    abstract::The use of four cyclodextrins (three native and one beta-CD derivative) as NMR chiral solvating agents to resolve the enantiomers of (+/-)-cizolirtine, 1, and its chemical precursor (the carbinol, (+/-)-2), was investigated. The best enantiodiscrimination occurred when beta-cyclodextrin was used. ROESY experiments wer...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:9<694::AID-CHIR5>3

    authors: Redondo J,Blázquez MA,Torrens A

    更新日期:1999-01-01 00:00:00

  • High-Performance Liquid Chromatographic Enantioseparation of Cyclic β-Amino Acids on Zwitterionic Chiral Stationary Phases Based on Cinchona Alkaloids.

    abstract::Stereoselective high-performance liquid chromatographic separations of eight sterically constrained cyclic β-amino acid enantiomer pairs were carried out using the newly developed Cinchona alkaloid-based zwitterionic chiral stationary phases Chiralpak ZWIX(+) and ZWIX(-). The effects of the mobile phase composition, t...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22458

    authors: Ilisz I,Gecse Z,Lajkó G,Forró E,Fülöp F,Lindner W,Péter A

    更新日期:2015-09-01 00:00:00

  • Enantioseparation of chiral perfluorooctane sulfonate (PFOS) by supercritical fluid chromatography (SFC): Effects of the chromatographic conditions and separation mechanism.

    abstract::Perfluorooctane sulfonate (PFOS) is one of the most frequently detected perfluoroalkyl substances in environmental and human samples. Previous studies have shown that nonracemic PFOS in biological samples can be used as a marker of PFOS exposure sources. In recent years, supercritical fluid chromatography (SFC) has em...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23120

    authors: Zhao L,Chen F,Guo F,Liu W,Liu K

    更新日期:2019-10-01 00:00:00

  • Cucurbituril: chiral applications.

    abstract::This review brings together the past and current methods for synthesizing the classical cucurbit[n]uril (Q[n]), structural variants, and derivatives. Here we refer to the first family of Q[n] as " classical," where the cavity is spheroidal and carry no substituents at any of the equatorial methine carbons or the methy...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22363

    authors: Mandadapu V,Day AI,Ghanem A

    更新日期:2014-11-01 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

  • Enantiomeric separation and simulation studies of pheniramine, oxybutynin, cetirizine, and brinzolamide chiral drugs on amylose-based columns.

    abstract::Solid phase extraction (SPE)-chiral separation of the important drugs pheniramine, oxybutynin, cetirizine, and brinzolamide was achieved on the C18 cartridge and AmyCoat (150 x 46 mm) and Chiralpak AD (25 cm x 0.46 cm id) chiral columns in human plasma. Pheniramine, oxybutynin, cetirizine, and brinzolamide were resolv...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22276

    authors: Ali I,Al-Othman ZA,Al-Warthan A,Alam SD,Farooqi JA

    更新日期:2014-03-01 00:00:00

  • Synthesis and pharmacological investigation of stereoisomeric muscarines.

    abstract::The synthesis of the eight stereoisomers of muscarine has been efficiently accomplished by utilizing the two enantiomers of lactic esters as starting material. The synthetic strategy is based on a SnCl4-catalyzed addition of allyltrimethylsilane to O-protected lactic aldehydes followed by an iodocyclization process. A...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530040406

    authors: De Amici M,Dallanoce C,De Micheli C,Grana E,Dondi G,Ladinsky H,Schiavi G,Zonta F

    更新日期:1992-01-01 00:00:00

  • Ion channels as pharmacologic receptors: the chirality of drug interactions.

    abstract::Ion channels are pharmacologic receptors and as such exhibit stereoselective interactions with drugs. Ion channels are conformationally mobile transmembrane proteins existing in a number of open and closed states. Drug interactions with these different states may differ quantitatively and qualitatively. Stereoselectiv...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/(SICI)1520-636X(1996)8:1<35::AID-CHIR8>3.0

    authors: Triggle DJ

    更新日期:1996-01-01 00:00:00

  • High-performance liquid chromatographic resolution of oxamniquine enantiomers: application to in vitro metabolism studies.

    abstract::A method is described for the HPLC analysis of oxamniquine enantiomers in liver fraction incubates, using a second-generation alpha 1-acid glycoprotein-based column (Chiral-AGP). Oxamniquine is extracted from the incubation media by liquid-liquid extraction, using diethyl ether. The dried residue is redissolved in elu...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530020413

    authors: Noctor TA,Fell AF,Kaye B

    更新日期:1990-01-01 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

  • 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

  • Plasmonic nanoparticles assemblies templated by helical bacteria and resulting optical activity.

    abstract::Plasmonic nanoparticles (NPs) adsorbing onto helical bacteria can lead to formation of NP helicoids with micron scale pitch. Associated chiroptical effects can be utilized as bioanalytical tool for bacterial detection and better understanding of the spectral behavior of helical self-assembled structures with different...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23225

    authors: Feng W,Kadiyala U,Yan J,Wang Y,DiRita VJ,VanEpps JS,Kotov NA

    更新日期:2020-07-01 00:00:00

  • Separation of Enantiomers of a Phospholipid in Langmuir Monolayers by a New Selector.

    abstract::Chiral discrimination in a racemic mixture of dipalmitoylphosphatidylcholine (DPPC) is induced by a new selector at the water-air interface: L-DPPC is segregated in the condensed phase of a Langmuir monolayer upon interactions with an enantiopure amphiphilic compound. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22508

    authors: Caminati G,Cicchi S,Lascialfari L,Brandi A

    更新日期:2015-11-01 00:00:00

  • Stereoselective Behavior of the Chiral Herbicides Diclofop-Methyl and Diclofop During the Soy Sauce Brewing Process.

    abstract::Chiral pesticides are now receiving more and more attention in the food-making process. This experiment studied the enantioselective behavior of diclofop-methyl (DM) and its main metabolite, diclofop (DC), during the soy sauce brewing process. Two kinds of commonly used strains, Aspergillus oryzae and Saccharomyces ro...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22545

    authors: Lu Y,Zhang D,Liao Y,Diao J,Chen X

    更新日期:2016-01-01 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

  • Enantiomer self-disproportionation and chiral stationary phase based selective chiral separation of organic compounds.

    abstract::In modern chromatography, chiral stationary phase (CSP) and enantiomer self-disproportionation (ESD) are new inventions of packing material offer a guarantee for a successful enantiomeric separation. All CSPs were synthesized by chemical bonding of the relevant organic moieties onto a porous parent silica material for...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20917

    authors: Mayani VJ,Abdi SH,Mayani SV,Kim HC,Park SK

    更新日期:2011-04-01 00:00:00

  • Enantiopurity determination of the enantiomers of the triple reuptake inhibitor indatraline.

    abstract::The present study describes the development of two approaches for the determination of the enantiopurity of both enantiomers of indatraline. Initially, a method was developed using different chiral solvating agents (CSAs) for diastereomeric discrimination regarding signal separation in (1)H nuclear magnetic resonance ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22235

    authors: Grimm SH,Allmendinger L,Höfner G,Wanner KT

    更新日期:2013-12-01 00:00:00

  • Two-dimensional separation of [7]helicene enantiomers on Cu(111).

    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

    authors: Ernst KH,Kuster Y,Fasel R,Müller M,Ellerbeck U

    更新日期:2001-01-01 00:00:00

  • Enantioselective LC/ESI-MS/MS analysis and pharmacokinetic and tissue distribution study of (2RS)-1-(7-methoxy-1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)-propan-2-ol in rats.

    abstract::A sensitive and stereospecific liquid chromatography-tandem mass spectrometry method for the quantitative determination of TWo8 enantiomers ((2RS)-1-(7-methoxy-1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)-propan-2-ol) was developed and validated in rat serum and some tissues. Racemic TWo8 is a new chemical ent...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22011

    authors: Walczak M,Szymura-Oleksia J,Groszek G

    更新日期:2012-08-01 00:00:00

  • Enantioselective separation of 1,4-disubstituted piperazine derivatives on two cellulose chiralcel OD and OJ and one amylose chiralpak AD chiral selectors

    abstract::A series of 1,4-disubstituted piperazine derivatives with hypnotic activity were examined on three polysaccharide-based chiral stationary phases, namely, Chiracel OD, Chiracel OJ and Chiralpak AD. It was possible to resolve all the compounds on all the phases examined (1.13

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:10<790::AID-CHIR9>

    authors: Chilmonczyk Z,Ksycinska H,Mazgajska M,Aboul-Enein HY

    更新日期:1999-01-01 00:00:00

  • A chiral enantioseparation generic strategy for anti-Alzheimer and antifungal drugs by short end injection capillary electrophoresis using an experimental design approach.

    abstract::The present study describes a generic strategy using capillary electrophoretic (CE) method for chiral enantioseparation of anti-Alzheimer drugs, namely, donepezil (DON), rivastigmine (RIV), and antifungal drugs, namely, ketoconazole (KET), Itraconazole (ITR), fluconazole (FLU), and sertaconazole (SRT) in which these d...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22777

    authors: Abdel-Megied AM,Hanafi RS,Aboul-Enein HY

    更新日期:2018-02-01 00:00:00

  • Simultaneous Chiral Separation of Flavanone, Naringenin, and Hesperetin Enantiomers by RP-UHPLC-DAD.

    abstract::A rapid and effective RP-UHPLC-DAD method for enantioseparation of three flavanones, i.e., flavanone, naringenin, and hesperetin, was developed and validated. Chromatographic separation of the analytes was performed using a Chiralpak AD-3R analytical column under reverse phase conditions with methanol as the mobile ph...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22559

    authors: Baranowska I,Hejniak J,Magiera S

    更新日期:2016-02-01 00:00:00