European Journal of Organic Chemistry

Cover image for Vol. 2013 Issue 3

January 2013

Volume 2013, Issue 3

Pages 411–616

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. You have free access to this content
      Synthesis of Monoconjugated and Multiply Conjugated Oligonucleotides by “Click Thiol” Thiol-Michael-Type Additions and by Combination with CuAAC “Click Huisgen” (Eur. J. Org. Chem. 3/2013)

      Albert Meyer, Jean-Jacques Vasseur and François Morvan

      Article first published online: 10 JAN 2013 | DOI: 10.1002/ejoc.201390003

      Thumbnail image of graphical abstract

      The cover picture shows that oligonucleotide conjugates with different biomolecules or markers could be obtained through the reaction between a thiol function of the oligonucleotide and an acrylamide function of the biomolecule or marker according to a Thiol-Michael-Type Addition (TMTA). This reaction could be combined sequentially with a Copper(I)-catalyzed Azide–Alkyne Cycloaddition (CuAAC) affording bis-conjugated oligonucleotides. These “click” reactions allow the preparation of a bouquet of molecules where their stem is a DNA sequence. This picture was inspirited by Picasso's “Bouquet with Hands”. The background is an autumn view of the countryside of Montpellier. Details are discussed in the article by F. Morvan et al. on p. 465 ff. The cover picture was elaborated by Thibault Morvan.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Graphical Abstract: Eur. J. Org. Chem. 3/2013 (pages 411–417)

      Article first published online: 10 JAN 2013 | DOI: 10.1002/ejoc.201390005

  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
  4. Microreview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. General Heterocycle Precursors

      Cascade Palladium- and Copper-Catalysed Aromatic Heterocycle Synthesis: The Emergence of General Precursors (pages 425–441)

      Catherine J. Ball and Michael C. Willis

      Article first published online: 11 DEC 2012 | DOI: 10.1002/ejoc.201201386

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      Over the last decade, four precursor types have been established as broadly general substrates in heterocycle synthesis. By appropriate choice of catalyst and coupling partner, these four precursor types can be converted into a wide range of aromatic products.

  5. Short Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. C–F Bond Activation

      Palladium-Catalyzed Base-Free Suzuki–Miyaura Coupling Reactions of Fluorinated Alkenes and Arenes via a Palladium Fluoride Key Intermediate (pages 443–447)

      Masato Ohashi, Hiroki Saijo, Mitsutoshi Shibata and Sensuke Ogoshi

      Article first published online: 29 NOV 2012 | DOI: 10.1002/ejoc.201201405

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      Pd0/PR3 complexes promote C–C bond formation with organoboronates through C–F bond activation of fluorinated alkenes. Mechanistic studies show that a PdII fluoride intermediate plays an essential role in this base-free cross-coupling reaction. Moreover, a Ni(NHC) catalyst is efficient for C–C coupling through C–F bond cleavage of fluoroarenes.

    2. Nitrogen Heterocycles

      Synthesis of the N-Substituted Pyridin-1(2H)-one Framework by Ligand-Assisted Pd-Catalyzed Reactions (pages 448–452)

      Kang Zhou, Ping Wen, Wenlin Chen, Chaowei Ma and Guosheng Huang

      Article first published online: 30 NOV 2012 | DOI: 10.1002/ejoc.201201151

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      An efficient ligand-assisted palladium-catalyzed approach for the straightforward synthesis of the pyridin-2(1H)-one framework was developed. This method provides one of the easiest pathways to access this class of valuable compounds from easily available starting materials (2-chloropyridines). A possible mechanism for this reaction is discussed.

    3. Biomimetic Synthesis

      Biomimetic Three-Component Assembly of the Central Core of Halichonadins K and L (pages 453–455)

      François Senejoux, Laurent Evanno and Erwan Poupon

      Article first published online: 10 DEC 2012 | DOI: 10.1002/ejoc.201201316

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      A one-pot multicomponent reaction involving the reaction of an isocyanide with an in situ generated dihydropyridinium salt permits a straightforward access to a biomimetic model of the recently isolated halichonadins K and L.

    4. Organocatalysis

      Organocatalytic Asymmetric Michael Addition of Oxazolones to Arylsulfonyl Indoles: Facile Access to syn-Configured α,β-Disubstituted Tryptophan Derivatives (pages 456–459)

      Chang-Wu Cai, Xing-Li Zhu, Song Wu, Zong-Le Zuo, Liang-Liang Yu, Da-Bin Qin, Quan-Zhong Liu and Lin-Hai Jing

      Article first published online: 30 NOV 2012 | DOI: 10.1002/ejoc.201201335

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      Organocatalytic asymmetric Michael addition of oxazolones 2 to vinylogous imine intermediates generated in situ from arylsulfonyl indoles 1 is described. This protocol provides facile access to optically active 3-indolyl derivatives with good results. The resulting adducts can be easily converted into syn-α,β-disubstituted tryptophan derivatives without compromising the stereoselectivities.

    5. Diaryl Selenides

      A Flexible Metal-Catalyzed Synthesis of Highly Substituted Aryl Phenanthrenyl Selenides (pages 460–464)

      Wontaeck Lim and Young Ho Rhee

      Article first published online: 10 DEC 2012 | DOI: 10.1002/ejoc.201201340

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      Highly substituted 9- and 10-selenylphenanthrenes are easily prepared from the corresponding selenium-containing (o-phenylaryl)alkynes. The selectivity is perfectly controlled by indium(III) and gold(I) catalysts. Various substrates can be converted into phenanthrene derivatives with high selectivity and in good yield under very mild conditions.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Oligonucleotide Conjugates

      Synthesis of Monoconjugated and Multiply Conjugated Oligonucleotides by “Click Thiol” Thiol-Michael-Type Additions and by Combination with CuAAC “Click Huisgen” (pages 465–473)

      Albert Meyer, Jean-Jacques Vasseur and François Morvan

      Article first published online: 4 DEC 2012 | DOI: 10.1002/ejoc.201201311

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      Oligonucleotide conjugates bearing different labels were synthesized by mono- or poly-Thiol Michael-Type Additions (TMTAs) through the use of acrylamide derivatives. Bis-oligonucleotide conjugates were obtained with a combination of TMTA and CuAAC “click” chemistry.

    2. Cycloadditions

      4-Alkenyl-2-aminothiazoles: Smart Dienes for Polar [4 + 2] Cycloadditions (pages 474–489)

      Mateo Alajarin, Jose Cabrera, Pilar Sanchez-Andrada, Raul-Angel Orenes and Aurelia Pastor

      Article first published online: 6 DEC 2012 | DOI: 10.1002/ejoc.201201185

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      4-Alkenyl-2-aminothiazoles act as in-out dienes in [4 + 2] cycloadditions with a wide variety of dienophiles. The reactions were endo-selective when cyclic dienophiles were used and regioselective with unsymmetrical dienophiles. A stepwise mechanism is proposed for the cycloadditions with acyclic dienophiles.

    3. Binaphthyl-Based Cycloheptanones

      Benzannulated Cycloheptanones from Binaphthyl Platforms (pages 490–497)

      Grégory Pieters, Kamal Sbargoud, Alexandre Bridoux, Anne Gaucher, Sylvain Marque, Flavien Bourdreux, Jérôme Marrot, David Flot, Guillaume Wantz, Olivier Dautel and Damien Prim

      Article first published online: 6 DEC 2012 | DOI: 10.1002/ejoc.201201370

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      Preparations of benzannulated cycloheptanones starting from binaphthyl molecular platforms are described.

    4. Two-Photon Chromophores

      Synthesis and Two-Photon Absorption Properties of Star-Shaped Chromophores Derived from Functionalized Fluorene Units (pages 498–508)

      Tzu-Chau Lin, Che-Yu Liu, Bor-Rong Huang, Ja-Hon Lin, Yu-Kai Shen and Cheng-Yu Wu

      Article first published online: 4 DEC 2012 | DOI: 10.1002/ejoc.201201236

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      A set of star-shaped chromophores containing functionalized fluorene units were synthesized and shown to possess ascending two-photon absorptivities with the growth of their π systems. The observed effective optical power-limiting and stabilization behaviors in the nanosecond time domain indicate that these dye molecules have potential as broadband and quick-responding optical limiters.

    5. Nitrogen-Rich Polymers

      Synthesis of Glycidyl-5-(carboxyethyl-1H-tetrazole)polymer and 1,2-Bis(5-carboxyethyl-1H-tetrazolyl)ethane as Polymeric Precursor (pages 509–514)

      Franziska M. Betzler, Thomas M. Klapötke and Stefan M. Sproll

      Article first published online: 4 DEC 2012 | DOI: 10.1002/ejoc.201201201

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      Synthesis of highly thermally stable energetic nitrogen-rich polymers incorporating tetrazole heterocycles and the corresponding polymer precursor is reported. Complete structural and spectroscopic characterization including IR and multinuclear NMR spectroscopy and mass spectrometry, as well as single-crystal X-ray diffraction analysis of 1,2-bis(5-carboxyethyl-1H-tetrazolyl)ethane, was accomplished.

    6. Cross-Coupling Reaction

      Efficient Manganese/Copper Bimetallic Catalyst for N-Arylation of Amides and Sulfonamides Under Mild Conditions in Water (pages 515–524)

      Yong-Chua Teo, Fui-Fong Yong, Idzham Khalid Ithnin, Siew-Hui Trionna Yio and Zhiyin Lin

      Article first published online: 30 NOV 2012 | DOI: 10.1002/ejoc.201201218

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      An efficient method using a bimetallic MnF2/CuI catalyst in combination with trans-1,2-diaminocyclohexane as the ligand has been developed for the cross-coupling of benzamides and sulfonamides with differently substituted aryl iodides in water. The corresponding N-arylated products were obtained in good to excellent yields (up to 97 %) under the catalytic conditions.

    7. Total Synthesis

      Total Synthesis of a 6,6-Spiroketal Metabolite, Dinemasone A (pages 525–532)

      Chada Raji Reddy, Boinapally Srikanth, Uredi Dilipkumar, Kakita Veera Mohana Rao and Bharatam Jagadeesh

      Article first published online: 27 NOV 2012 | DOI: 10.1002/ejoc.201201246

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      The stereoselective total synthesis of dinemasone A was accomplished in a longest linear sequence of 14 steps using double-intramolecular hetero-Michael addition as the key spiroketalisation reaction.

    8. Vinyl Sulfides and Vinylamines

      Synthesis of Vinyl Sulfides and Vinylamines through Catalytic Intramolecular Hydroarylation in the Presence of FeCl3 and AgOTf (pages 533–540)

      Dahan Eom, Juntae Mo, Phil Ho Lee, Zhiming Gao and Sunggak Kim

      Article first published online: 30 NOV 2012 | DOI: 10.1002/ejoc.201201270

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      A synthetic method was developed for the preparation of vinyl sulfides and vinylamines. Arylalkynyl phenyl sulfides and sulfonamides underwent a catalytic intramolecular hydroarylation reaction to give 1,2-dihydronaphthalenes, 2H-chromenes, and 1,2-dihydroquinolines with a phenylsulfenyl or N-phenyl-N-tosyl group on the sp2-hybridized benzylic carbon.

    9. Pyridinophane Synthesis

      Synthesis of Planar Chiral N-Heterocyclic-Substituted Pyridinophanes (pages 541–549)

      Joshua J. P. Kramer, Martin Nieger and Stefan Bräse

      Article first published online: 27 NOV 2012 | DOI: 10.1002/ejoc.201201286

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      New planar chiral bis(heterocyclic) N-donors based on the rarely investigated class of [2](1,4)-benzene[2](2,5)pyridinophanes were synthesized. The synthesis of the pyridinophane scaffold was simplified, and a pyrazole, triazole, tetrazole, and pyrimidine heterocycle were successfully attached to the planar chiral backbone.

    10. Fluorescent Arylalanine Derivatives

      Synthesis of Fluorescent Alanines by a Rhodium-Catalysed Conjugate Addition of Arylboronic Acids to Dehydroalanine Derivatives (pages 550–556)

      Paula M. T. Ferreira, Luís S. Monteiro, Goreti Pereira, Elisabete M. S. Castanheira and Christopher G. Frost

      Article first published online: 29 NOV 2012 | DOI: 10.1002/ejoc.201201198

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      Fluorescent β-arylalanine derivatives were prepared in good yields using a rhodium-catalysed conjugate addition of arylboronic acids to N-protected dehydroalanines. The photophysical properties of some of the β-arylalanines were studied in solvents of different polarities. Considering the high fluorescence quantum yield of these compounds, some of them may be useful as fluorescent markers.

    11. Enantioselective Resolution

      Carica papaya Lipase Catalysed Resolution of β-Amino Esters for the Highly Enantioselective Synthesis of (S)-Dapoxetine (pages 557–565)

      Pengyong You, Jian Qiu, Erzheng Su and Dongzhi Wei

      Article first published online: 7 DEC 2012 | DOI: 10.1002/ejoc.201201055

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      A carica papaya lipase catalysed resolution of N-protected β-phenylalanine esters has been developed. High enantioselectivity was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. After 50 % conversion, the products were separated and used as key chiral intermediates for the synthesis of (S)-dapoxetine with > 99 % ee.

    12. Alkene Metathesis

      Self-Metathesis of Polyol Allyl Ethers towards Carbohydrate-Based Oligohydroxy Derivatives (pages 566–577)

      Maike Tober and Joachim Thiem

      Article first published online: 7 DEC 2012 | DOI: 10.1002/ejoc.201201083

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      Various allyl ethers of 1,4-anhydro-D-sorbitol and pentaerythritol underwent self-metathesis reactions to give oligohydroxy dimers useful as new components for alkyd resin formation.

    13. Natural Product Synthesis

      Stereodivergent Total Synthesis of (+)-Aspergillide B and (+)-7-epi-Aspergillide A (pages 578–587)

      Y. Sridhar and P. Srihari

      Article first published online: 27 NOV 2012 | DOI: 10.1002/ejoc.201201155

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      The stereoselective total syntheses of (+)-aspergillide B and (+)-7-epi-aspergillide A were achieved. The key reactions include Noyori's asymmetric transfer hydrogenation, an Achmatowicz rearrangement, a Ferrier-type alkynylation, a hydrosilylation–protodesilylation, a CBS (Corey–Bakshi–Shibata) oxazaborolidine reduction, a Yamaguchi macrolactonization, and a Mitsunobu macrolactonization.

      Corrected by:

      Correction: Stereodivergent Total Synthesis of (+)-Aspergillide B and (+)-7-epi-Aspergillide A

      Vol. 2014, Issue 7, 1557, Article first published online: 28 JAN 2014

    14. Organocatalysis

      Chitosan Aerogel Beads as a Heterogeneous Organocatalyst for the Asymmetric Aldol Reaction in the Presence of Water: An Assessment of the Effect of Additives (pages 588–594)

      Claudio Gioia, Alfredo Ricci, Luca Bernardi, Khadidja Bourahla, Nathalie Tanchoux, Mike Robitzer and Françoise Quignard

      Article first published online: 27 NOV 2012 | DOI: 10.1002/ejoc.201201187

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      Chitosan aerogel, derived from the abundant natural biopolymer chitin, has been used as a heterogeneous amine catalyst for the asymmetric aldol reaction in water. The combination of fatty acids and surfactants as additives in the reaction had a strikingly beneficial effect on the reaction outcome, especially when heterocyclic ketones were used as donors.

    15. Glycosides

      A One-Pot, Copper-Catalyzed Cascade Route to 2-Indolyl-C-glycosides (pages 595–604)

      Parthasarathi Subramanian and Krishna P. Kaliappan

      Article first published online: 30 NOV 2012 | DOI: 10.1002/ejoc.201201208

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      An efficient and high-yielding, one-pot, Cu-catalyzed synthesis of 2-indolyl-C-glycosides is delineated. The sequence involves a cascade Sonogashira type coupling and a hydroamination reaction between sugar-derived alkynes and N-tosyl-o-iodoaniline followed by the removal of the N-tosyl group to provide a library of 2-indolyl-C-glycosides in moderate to excellent yields.

    16. Samarium-Mediated Reduction

      Samarium Diiodide Promoted Reduction of 3,6-Dihydro-2H-1,2-oxazines: Competition of 1,4-Amino Alcohol Formation and Ring Contraction to Pyrrole Derivatives (pages 605–610)

      Marcin Jasiński, Toshiko Watanabe and Hans-Ulrich Reissig

      Article first published online: 5 DEC 2012 | DOI: 10.1002/ejoc.201201210

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      The samarium diiodide promoted reduction of 3,6-dihydro-2H-1,2-oxazine derivatives not only provides the expected acyclic 1,4-amino alcohols but also electron-rich pyrroles. The latter products are formed by a surprising ring contraction that probably involves an intramolecular hydrogen shift.

    17. Conformational Analysis

      Elucidation of the Forces Governing the Stereochemistry of Biphenyl (pages 611–616)

      Jianfeng Jia, Hai-Shun Wu, Zhenhua Chen and Yirong Mo

      Article first published online: 4 DEC 2012 | DOI: 10.1002/ejoc.201201273

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      The twist conformation in biphenyl results from a balance between the stabilization arising from electron delocalization, which favors a planar structure, and steric repulsion, which favors a perpendicular structure. The two competing forces have nearly the same magnitude.

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