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  • 1.
    Ahlford, Katrin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zaitsev, Alexey B.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ekström, Jesper
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A Simple and Efficient Catalyst System for the Asymmetric Transfer Hydrogenation of Ketones2007In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, no 16, p. 2541-2544Article in journal (Refereed)
  • 2.
    Ali, Tara
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Structural Studies of O-Polysaccharides from Diarrhoeal Escherichia coli2007Doctoral thesis, monograph (Other academic)
    Abstract [en]

    This thesis describes the structural analysis of O-polysaccharides from the Gram-negative bacterium Escherichia coli that is a diarrhoeal pathogen. The Escherichia coli serotypes investigated were O178, O171, O166 and O128. The methods used in these studies were nuclear magnetic resonance spectroscopy and component analysis.

    All analysed serotypes had pentasaccharide repeating units. E. coli strain O128 and O166 was shown to have the topology of four carbohydrate residues in the backbone while the 5-residue backbone is found in E. coli O178 and O171.

    The biological repeating units have been determined for the analysed polysaccharides and it was shown that all of the serotypes studied had a 3-substituted N-acetylgalactosamine residue at the reducing end. From this it was deduced that the terminal end of E. coli O171 and O128 have sialic acid and blood type antigens, respectively. This should make E. coli O171 and O128 less recognizable to the immune system as a foreign invader. This can result in that E. coli O171 and O128 may evade the immune system more easily.

  • 3.
    Ali, Tara
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Weintraub, Andrej
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Structural determination of the O-antigenic polysaccharide from Escherichia coli O1662007In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 342, no 2, p. 274-278Article in journal (Refereed)
  • 4.
    Andersson, Nina
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Mesostructured materials: Synthesis towards applications2007Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    A new class of materials with well-defined structures on mesoscopic (2-50 nm) length scales has attracted considerable interest during the last decade. These mesostructured mataterials are formed from the self-assembly of amphiphillic molecules and inorganic precursors. The aim of this thesis has been to develop preparation methods that are scalable, and at the same time allow for efficient structural control coupled with possibility to incorporate different functionalities.

    Two different industrial processes for production of particles with spherical morphology were successfully tailored for synthesis of well-ordered mesostructured particles. An existing spray drying method for a fast and continuous production was further developed, and for the first time, an emulsion-based method was implemented. The latter method resulted in superior control of both particle size and internal mesostructure.

    Mesostructured photochromic pigments were synthesised by incorporating photochromic dyes in the organic domains of the surfactant templated inorganic/organic mesostructured silica particles. The pigments were produced using a one-pot synthesis method employing an aerosol reactor, allowing control over both the internal mesostructure and the dye content. We show that transparent photochromic films can be prepared using latex binders and conventional coating technology.

    Mesoporous magnetic carrier materials were prepared by adding iron oxide nanoparticles during either the emulsion- or aerosol processing. The surfactant templated silica matrix displayed well-ordered internal pore architecture with limited pore blocking caused by the incorporated iron oxide nanoparticles. The iron oxide content was precisely controlled, and the magnetic properties were preserved during the processing. Finally we demonstrate that these materials can be used to magnetically separate water-soluble dyes from solution.

  • 5. Back, Marcus
    et al.
    Nyhlén, Jonas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kvarnström, Ingemar
    Rosenquist, Åsa
    Samuelsson, Bertil
    Design, synthesis and SAR of potent statin-based β-secretase inhibitors: Exploration of P1 phenoxy and benzyloxy residues2007Conference paper (Other academic)
  • 6.
    Bielawski, Marcin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    High-Yielding One-Pot Synthesis of Diaryliodonium Triflates from Arenes and Iodine or Aryl Iodides2007In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, no 24, p. 2521-2523Article in journal (Refereed)
    Abstract [en]

    Unsymmetric and symmetric diaryliodonium triflates are synthesized from both electron-deficient and electron-rich substrates in a fast, high yielding, and operationally simple protocol employing arenes and aryl iodides or iodine.

  • 7.
    Bielawski, Marcin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Mingzhao
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient and General One-Pot Synthesis of Diaryliodonium Triflates: Optimization, Scope and Limitations2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, no 17-18, p. 2610-2618Article in journal (Refereed)
    Abstract [en]

    Symmetrical and unsymmetrical diaryliodonium triflates have been synthesized from both electron-deficient and electron-rich arenes and aryl iodides with mCPBA and triflic acid. A thorough investigation of the optimization, scope and limitations has resulted in an improved one-pot protocol that is fast, high-yielding, and operationally simple. The reaction has been extended to the direct synthesis of symmetrical iodonium salts from iodine and arenes, conveniently circumventing the need for aryl iodides.

  • 8.
    Bielawski, Marcin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Mingzhao
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient and general one-pot synthesis of diaryliodonium triflates: scope and limitations2007In: SIS Report: The 10th Symposium on Iodine Science, Chiba University, Japan 2007, 2007, p. 19-22Conference paper (Other academic)
  • 9.
    Bogár, Krisztián
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthetic Transformations via Metal- and Enzyme-Catalyzed Dynamic Kinetic Resolution2007Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis deals with the preparation of a new half-sandwich type ruthenium(II)- catalyst for racemization of optically active secondary alcohols and the development of a highly efficient method in combination with lipases such as Candida antarctica lipase B and Pseudomonas cepacia lipase for dynamic kinetic resolution of various functionalized alcohols under mild reaction conditions.

    It was shown that the RuCl(CO)25-C5Ph5) complex can racemize optically active aliphatic and aromatic secondary alcohols at room temperature in rather short times. Different parameters, such as the nature of the catalyst, catalyst loading and solvent effect were studied. After the optimization steps, the Ru-catalyzed racemization of (S)-1-phenylethanol in the presence of Candida antarctica lipase B was also investigated. The compatibility of the metal- and enzyme-catalyzed reactions led to a highly efficient coupled catalytic system for transformation of racemic alcohols to their enantiomerically pure acetates. This protocol was applied for a wide range of secondary alcohols. It was shown that in the case of allylic alcohols the obtained enantiopure allylic acetates are useful compounds for synthesis of α-methyl carboxylic acids such as (R)-Flurbiprofen and acyloin acetates. Highly selective dynamic kinetic asymmetric transformation of 3,5-piperidine diol to deliver various 3,5-dioxygenated piperidines is also described.

  • 10.
    Bogár, Krisztián
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    High-yielding metalloenzymatic dynamic kinetic resolution of fluorinated aryl alcohols2007In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 48, no 31, p. 5471-5474Article in journal (Refereed)
    Abstract [en]

    Dynamic kinetic resolution (DKR) of various fluorinated aryl alcohols by a combination of lipase-catalyzed enzymatic resolution with in situ ruthenium-catalyzed alcohol racemization is described. (R)-Selective Candida antarctica lipase B (CALB) was employed for transesterification of different fluoroaryl alcohols in DKR reactions delivering the corresponding acetates in high yield (97%) with excellent enantiomeric excess (98%).

  • 11.
    Bogár, Krisztián
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hoyos Vidal, Pilar
    Alcántara León, Andrés R.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chemoenzymatic Dynamic Kinetic Resolution of Allylic Alcohols: A Highly Enantioselective Route to Acyloin Acetates2007In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 9, no 17, p. 3401-3404Article in journal (Refereed)
    Abstract [en]

    Dynamic kinetic resolution (DKR) of a series of sterically hindered allylic alcohols has been conducted with Candida antarctica lipase B (CALB) and ruthenium catalyst 1. The optically pure allylic acetates obtained were subjected to oxidative cleavage to give the corresponding acylated acyloins in high yields without loss of chiral information.

  • 12. Bogár, Krisztián
    et al.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Large-scale ruthenium- and enzyme-catalyzed dynamic kinetic resolution of (rac)-1-phenylethanol2007In: Beilstein Journal of Organic Chemistry, ISSN 1860-5397, Vol. 3, p. artikel nr 50-Article in journal (Refereed)
  • 13. Carballeira, José Daniel
    et al.
    Krumlinde, Patrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bocola, Marco
    Vogel, Andreas
    Reetz, Manfred T.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Directed evolution and axial chirality: optimization of the enantioselectivity of Pseudomonas aeruginosa lipase towards the kinetic resolution of a racemic allene2007In: Chemical Communications, ISSN 1359-7345, Vol. 20, p. 1913-1915Article in journal (Refereed)
  • 14.
    Ekström, Jesper
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Transition Metal Hydrides: Biomimetic Studies and Catalytic Applications2007Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    In this thesis, studies of the nature of different transition metal-hydride complexes are described. The first part deals with the enantioswitchable behaviour of rhodium complexes derived from amino acids, applied in asymmetric transfer hydrogenation of ketones. We found that the use of amino acid thio amide ligands resulted in the formation of the R-configured product, whereas the use of the corresponding hydroxamic acid- or hydrazide ligands selectively gave the S-alcohol.

    Structure/activity investigations revealed that the stereochemical outcome of the catalytic reaction depends on the ligand mode of coordination.

    In the second part, an Fe hydrogenase active site model complex with a labile amine ligand has been synthesized and studied. The aim of this study was to find a complex that efficiently catalyzes the reduction of protons to molecular hydrogen under mild conditions. We found that the amine ligand functions as a mimic of the loosely bound ligand which is part of the active site in the hydrogenase.

    Further, an Fe hydrogenase active site model complex has been coupled to a photosensitizer with the aim of achieving light induced hydrogen production. The redox properties of the produced complex are such that no electron transfer from the photosensitizer part to the Fe moiety occurs.

    In the last part of this thesis, the development of a protocol for the transfer hydrogenation of ketones to secondary alcohols without the involvement of transition metal catalysts is described. A variety of ketones were efficiently reduced in 2-propanol using catalytic amounts of alkali alkoxide under microwave irradiation.

  • 15.
    Ekström, Jesper
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wettergren, Jenny
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A Simple and Efficient Catalytic Method for the Reduction of Ketones2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, no 10, p. 1609-1613Article in journal (Refereed)
    Abstract [en]

    A range of ketones was efficiently reduced in the presence of catalytic amounts of lithium isopropoxide in 2-propanol under microwave heating, with alcohol products being formed in yields up to 99 %.

  • 16.
    Frigell, Jens
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    First synthesis of 4a-carba-beta-D-galactofuranose2007In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 48, no 52, p. 9073-9076Article in journal (Refereed)
  • 17.
    Ibrahem, Ismail
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Development of organocatalytic asymmetric transformations2007Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The ability of amino acids and amino acid derivatives to mediate various organocatalytic asymmetric transformations has been investigated and applied in the development of various reactions. This work describes the development of a direct catalytic asymmetric α-aminomethylation of ketones and aldehydes, a catalytic asymmetric aziridination, hydrophosphination and amination of α,β-unsaturated aldehydes.

  • 18.
    Ibrahem, Ismail
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramon
    Vesely, Jan
    Hammar, Peter
    Eriksson, Lars
    Himo, Fahmi
    Cordova, Armando
    Enantioselective Organocatalytic Hydrophosphination of α,β- Unsaturated Aldehydes2007In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, p. 4507-Article in journal (Refereed)
  • 19.
    Ibrahem, Ismail
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramon
    Vesely, Jan
    Zhao, Guiling
    Cordova, Armando
    Organocatalytic Asymmetric 5-Hydroxyisoxazolidine Synthesis: A Highly Enantioselective Route to β-Amino Acids2007In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, p. 849-852Article in journal (Refereed)
  • 20.
    Ibrahem, Ismail
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramón
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vesely, Jan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hammar, Peter
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Himo, Fahmi
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantioselective organocatalytic hydrophosphination of alpha,beta-unsaturated aldehydes2007In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, p. 4507-4510Article in journal (Refereed)
  • 21.
    Ibrahem, Ismail
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Guiling
    Cordova, Armando
    Direct Catalytic Enantioselective α-Aminomethylation of Aldehydes2007In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 13, p. 683-Article in journal (Refereed)
  • 22.
    Mannerstedt, Karin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ekelöf, Kerstin
    Oscarson, Stefan
    Evaluation of Thioglycosides of Kdo as Glycosyl Donor2007In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 342, no 3-4, p. 631-637Article in journal (Refereed)
    Abstract [en]

    The use of Kdo thioglycosides as glycosyl donors using DMTST, IBr/AgOTf and NIS/AgOTf as promoters has been evaluated. Activation at low temperature allowed to escape the formation of 2,3-glycal byproducts to give glycosides in high yield and with good β-anomeric selectivity. The use of diethyl ether as solvent and (especially) isopropylidene acetals as protecting groups improved the α-anomeric selectivity. NIS/AgOTf as promoter surprisingly yielded the 3-iodo-product via the glycal intermediate.

  • 23.
    Norinder, Jakob
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bogár, Krisztián
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kanupp, Lisa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    An enantioselective route to alpha-methyl carboxylic acids via metal and enzyme catalysis2007In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 9, no 24, p. 5095-5098Article in journal (Refereed)
    Abstract [en]

    Dynamic kinetic resolution of allylic alcohols to allylic acetates followed by copper-catalyzed allylic substitution gave alkenes in high yields and high optical purity. Subsequent oxidative C-C double bond cleavage afforded pharmaceutically important alpha-methyl substituted carboxylic acids in high ee.

  • 24.
    Norinder, Jakob
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dynamic processes in the copper-catalyzed substitution of chiral allylic acetates leading to loss of chiral information2007In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 13, p. 4094-4102Article in journal (Refereed)
    Abstract [en]

    Copper-catalyzed α-substitution of enantiomerically pure secondary allylic esters with Grignard reagents was studied with the aim to find conditions that give racemic products. It was observed that the degree of chiral transfer is strongly dependent on the temperature. The loss of chiral information is consistent with an equilibration of the CuIII(allyl) intermediates prior to product formation. Equilibration of the reaction intermediates is of importance for a possible development of a dynamic kinetic asymmetric transformation (DYKAT) process, in which a chiral catalyst is used to produce an optically active product from a racemic substrate, by means of a dynamic equilibrium of the diastereomeric reaction intermediates.

  • 25.
    Piera, Julio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Persson, Andreas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Caldentey, Xisco
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Water as nucleophile in palladium-catalyzed oxidative carbohydroxylation of allene-substituted conjugated dienes2007In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 129, no 46, p. 14120-14121Article in journal (Refereed)
    Abstract [en]

    An efficient palladium(II)-catalyzed oxidative carbohydroxylation of allene-substituted conjugated dienes in aqueous media has been developed. The reaction is conducted employing p-benzoquinone as the stoichiometric reoxidant for the palladium or under aerobic conditions with essentially the same outcome. It is worth mentioning that this is the first example of a palladium(II)-catalyzed oxidation where a carbon−carbon bond is formed in water and also one of the few cases of nucleophilic attack by water on a (π-allyl)palladium complex.

  • 26. Pozo-Gonzalo, Cristina
    et al.
    Pomposo, Jose A.
    Rodriguez, Javier
    Schmidt, Elena Yu.
    Vasil'tsov, Alexander M.
    Zorina, Nadezhda V.
    Ivanov, Andrey V.
    Trofimov, Boris A.
    Mikhaleva, Al'bina I.
    Zaitsev, Alexey B.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis and electrochemical study of narrow band gap conducting polymers based on 2,2 '-dipyrroles linked with conjugated aza-spacers2007In: Synthetic metals, ISSN 0379-6779, E-ISSN 1879-3290, Vol. 157, no 1, p. 60-65Article in journal (Refereed)
    Abstract [en]

    A series of 2,2'-dipyrrole monomers separated by aza-spacers (N,N'-bis-(1H-pyrrol-2-ylmethylene)-benzene-1,4-diamine; N-4,N-4'-bis(1H-pyrrol-2-ylmethylene)-biphenyl-4,4'-diamine; N,N'-bis-[1-(1H-pyrrol-2-yl)-ethylidene]-hydrazine; and 4,4'-bis[(1H-pyrrol-2-yl)-diazenyl] biphenyl) have been synthesised using modified Schiff and azo-coupling reactions. The new 2,2'-dipyrroles linked with conjugated aza-spacers have been evaluated as precursors of narrow band gap conducting polymers. Electrochemically synthesized poly(N,N'-bis-[1-(1H-pyrrol-2-yl)ethylidene]-hydrazine) displays a narrow band gap of just 0.7 eV, making it a suitable candidate for optoelectronic applications.

  • 27.
    Rios, Ramón
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sundén, Henrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vesely, Jan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A simple organocatalytic enantioselective cyclopropanation of alpha-beta-unsaturated aldehydes2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, p. 1028-1032Article in journal (Refereed)
  • 28.
    Slättegård, Rikard
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of Structures Related to the Capsular Polysaccharide of Neisseria meningitidis Serogroup A and to Mycothiol2007Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis describes the synthesis of structures related to the capsular polysaccharide of Neisseria meningitidis serogroup A and the synthesis of analogues of mycothiol, a compound produced by Mycobacterium tuberculosis. The first part of the thesis describes the synthesis of structural elements present in the native capsular polysaccharide of Neisseria meningitidis serogroup A. In this part, an improved synthesis of 2-azido-2-deoxy-D-mannopyranose is included. The second part of the thesis describes the formation of stable C-phosphonate analogues related to the capsular polysaccharide. The last part outlines the formation of analogues of mycothiol, where the syntheses of a bicyclic analogue and a thioglycosidic analogue are described.

  • 29.
    Stamatov, Stephan D.
    et al.
    -.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry. -.
    Regioselective and stereospecific opening of an oxirane system mediated by trifluoroacetic acid and halide anions. A new direct approach to C3-vicinal halohydrins.: -2007In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, ISSN -, Vol. 48, no -, p. 1887-1889Article in journal (Refereed)
    Abstract [en]

    -

  • 30.
    Strübing, Dirk
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Krumlinde, Patrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Piera, Julio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dynamic kinetic resolution of primary alcohols with an unfunctionalized stereogenic center in the beta-position2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, p. 1577-1581Article in journal (Refereed)
  • 31.
    Sundén, Henrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Organocatalytic Domino Reactions2007Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Organocatalyzed reactions involving activation strategies of ketones and aldehydes are important processes in organic chemistry. These activation strategies serve as a versatile platform for the construction of several domino reactions. This thesis describes the development of six new asymmetric or-ganocatalyzed domino reactions for the enantioselective formation of carbo-cycles or heterocycles. The domino reactions are based on two major activation pathways the domino “iminium-enamine” and the domino “enamine-iminium”. Making use of the domino “iminium-enamine” reaction, 2H-1-benzopyrans, 2H-1-benzothiopyrans and 1,2-dihydroquinolines and cyclopropanes can be obtained in high yields and excellent ee´s. Via the amine-catalyzed domino “enamine-iminium” reaction the synthesis of aza-Diels-Alder and Diels-Alder products can be achieved with high ee´s and yields. Moreover, a mechanistic model is proposed for each reaction that enables the stereochemical outcome of the reaction to be predicted.

  • 32.
    Sundén, Henrik
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramón
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A highly enantioselective catalytic domino aza-Michael/aldol reaction: one-pot organocatalytic asymmetric synthesis of 1,2-dihydroquinolidines2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, p. 827-832Article in journal (Refereed)
  • 33. Vesely, Jan
    et al.
    Ibrahem, Ismail
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Guiling
    Rios, Ramon
    Cordova, Armando
    Organocatalytic Enantioselective Aziridination of α,β-Unsaturated Aldehydes2007In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, p. 778-Article in journal (Refereed)
  • 34.
    Vesely, Jan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramón
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Organocatalytic enantioselective aziridination of alpha,beta-unsaturated aldehydes2007In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, p. 778-781Article in journal (Refereed)
  • 35. Wang, Zhen
    et al.
    Liu, Jian-Hui
    He, Cheng-Jiang
    Jiang, Shi
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Li-Cheng
    Azadithiolates cofactor of the iron-only hydrogenase and its PR3-monosubstituted derivatives: Synthesis, structure, electrochemistry and protonation2007In: Journal of Organometallic Chemistry, ISSN 0022-328X, E-ISSN 1872-8561, Vol. 692, no 24, p. 5501-5507Article in journal (Refereed)
    Abstract [en]

    The core structure (mu-SCH2)(2)NH[Fe-2(CO)(6)](5) of Fe-only hydrogenases active site model has been synthesized by the condensation of iron carbonyl sulfides, formaldehyde and silyl protected amine. Its monosubstituted complexes (mu-SCH2)(2)NH[Fe-2(CO)(5)PR3] (R = Ph (6), Me (7)) were accordingly prepared. The coordination configurations of 5 and 6 were characterized by X-ray crystallography. Protonation of complex 7 to form the N-protonated product occurs in an acetonitrile solution upon addition of triflic acid. The redox properties of these model complexes were studied by cyclic voltammetry.

  • 36. Wang, Zhen
    et al.
    Liu, Jianhui
    He, Chengjiang
    Jiang, Shi
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    Diiron azadithiolates with hydrophilic phosphatriazaadamantane ligand as iron-only hydrogenase active site models: Synthesis, structure, and electrochemical study2007In: Inorganica Chimica Acta, ISSN 0020-1693, E-ISSN 1873-3255, Vol. 360, no 7, p. 2411-2419Article in journal (Refereed)
    Abstract [en]

    Three novel complexes (mu-adt)[Fe-2(CO)(5)PTA] (2-PTA), (mu-adt)[Fe-2(CO)(4)PTA(2)](2-PTA(2)) and (mu-adt)[Fe-2(CO)(5)DAPTA] (2-DAPTA), where adt is SCH2N(CH2CH2CH3)CH2S, PTA stands for 1,3,5-triaza-7-phosphaadamantane and DAPTA is 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane, were prepared as the models of the iron hydrogenase active site through controlled CO displacement of (mu-adt)[Fe-2(CO)(6)] with PTA and DAPTA. The coordination configurations of 2-PTA and 2-PTA(2) were characterized by X-ray crystallography. The disubstituted diiron complex 2-PTA(2) features a basal/apical coordination mode, instead of the typical transoid basal/basal configuration. Protonation of three complexes only occurred at the bridging-N atom, rather than at the tertiary nitrogen atom on the PTA or DAPTA ligands. Electrochemical properties of the complexes were studied in acetonitrile or a mixture of acetonitrile and water in the presence of acetic acid, by cyclic voltammetry. The current sensitivity of the reduced species to acid concentration in the presence of H2O is greater than in the pure CH3CN solution.

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