European Journal of Organic Chemistry

Cover image for Vol. 2011 Issue 20‐21

Special Issue: Women in Chemistry

July 2011

Volume 2011, Issue 20-21

Pages 3541–4052

Issue edited by: Jennifer O'Donnell

  1. Cover Picture

    1. Top of page
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    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profiles
    8. Profile
    9. Microreviews
    10. Short Communications
    11. Full Papers
    1. (Eur. J. Org. Chem. 20-21/2011)

      Article first published online: 12 JUL 2011 | DOI: 10.1002/ejoc.201190051

  2. Back Cover

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    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profiles
    8. Profile
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    10. Short Communications
    11. Full Papers
    1. (Eur. J. Org. Chem. 20-21/2011)

      Article first published online: 12 JUL 2011 | DOI: 10.1002/ejoc.201190052

  3. Editorial

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    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profiles
    8. Profile
    9. Microreviews
    10. Short Communications
    11. Full Papers
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  4. Graphical Abstract

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    4. Editorial
    5. Graphical Abstract
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    11. Full Papers
    1. Graphical Abstract: Eur. J. Org. Chem. 20-21/2011 (pages 3543–3556)

      Article first published online: 12 JUL 2011 | DOI: 10.1002/ejoc.201190054

  5. News

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  6. Author Profiles

    1. Top of page
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      Janine COSSY (page 3562)

      Article first published online: 20 JUN 2011 | DOI: 10.1002/ejoc.201100863

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      Karola RÜCK-BRAUN (page 3563)

      Article first published online: 20 JUN 2011 | DOI: 10.1002/ejoc.201100864

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      Isabel ARENDS (page 3564)

      Article first published online: 20 JUN 2011 | DOI: 10.1002/ejoc.201100865

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      Annemieke MADDER (page 3565)

      Article first published online: 20 JUN 2011 | DOI: 10.1002/ejoc.201100866

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      Carmen NÁJERA (page 3566)

      Article first published online: 20 JUN 2011 | DOI: 10.1002/ejoc.201100867

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  7. Profile

    1. Top of page
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    4. Editorial
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    1. Women in EurJOC (Eur. J. Org. Chem. 20-21/2011) (pages 3567–3579)

      Article first published online: 12 JUL 2011 | DOI: 10.1002/ejoc.201190056

  8. Microreviews

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    1. Mannose-Specific Bacterial Adhesion

      The Bacterial Lectin FimH, a Target for Drug Discovery – Carbohydrate Inhibitors of Type 1 Fimbriae-Mediated Bacterial Adhesion (pages 3583–3609)

      Mirja Hartmann and Thisbe K. Lindhorst

      Article first published online: 15 JUN 2011 | DOI: 10.1002/ejoc.201100407

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      FimH is a well-investigated lectin, which is used by bacteria to adhere to glycosylated surfaces, such as cells. This microreview gives an overview of the development of FimH ligands, structural properties of the lectin and in vitro testing methods applied in the screen for putative inhibitors of type 1 fimbriae-mediated bacterial adhesion.

    2. N-Acyliminium Ions

      Strategies Based on Aryllithium and N-Acyliminium Ion Cyclizations for the Stereocontrolled Synthesis of Alkaloids and Related Systems (pages 3610–3633)

      Unai Martínez-Estibalez, Asier Gómez-SanJuan, Oihane García-Calvo, Eider Aranzamendi, Esther Lete and Nuria Sotomayor

      Article first published online: 13 MAY 2011 | DOI: 10.1002/ejoc.201100123

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      Intramolecular α-amidoalkylation reactions of aromatic rings and tandem Parham cyclization/intermolecular α-amidoalkylation constitute versatile synthetic tools that have been applied for the stereoselective synthesis of heterocyclic skeletons. Recent developments of synthetic methods based on these reactions are reviewed, with special attention to stereoselectivity.

    3. Metathesis

      Progress in Metathesis Through Natural Product Synthesis (pages 3634–3647)

      Joëlle Prunet

      Article first published online: 1 JUN 2011 | DOI: 10.1002/ejoc.201100442

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      This review (which is not comprehensive) covers progress in the area of metathesis that has been prompted by the difficulties encountered in use of these reactions in the course of the synthesis of natural products.

    4. Foldamers

      Foldamers Based on Oxazolidin-2-ones (pages 3648–3669)

      Claudia Tomasini, Gaetano Angelici and Nicola Castellucci

      Article first published online: 22 JUN 2011 | DOI: 10.1002/ejoc.201100493

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      The synthesis and conformation analysis of foldamers containing oxazolidin-2-one units are reported, together with some studies of their use as supramolecular materials. The synthetic approach is highly tuneable with endless variations, so a wide variety of foldamers with the required properties both in solution and in the solid state may be easily prepared “on demand”.

  9. Short Communications

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    1. Alcohol Allylation

      Calcium-Catalyzed Direct Coupling of Alcohols with Organosilanes (pages 3671–3674)

      Vera J. Meyer and Meike Niggemann

      Article first published online: 29 MAR 2011 | DOI: 10.1002/ejoc.201100231

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      A calcium-catalyzed direct substitution of π-activated alcohols, such as secondary and tertiary allylic, secondary benzylic, and tertiary propargylic alcohols, with different types of organosilanes under very mild reaction conditions is presented. Furthermore, the first direct substitution of an alcohol with (E)- as well as (Z)-alkenylsilanes was achieved under mild reaction conditions.

    2. Asymmetric Catalysis

      Catalytic Asymmetric α-Chlorination of 3-Acyloxazolidin-2-one with a Trinary Catalytic System (pages 3675–3678)

      Yoshitaka Hamashima, Tatsuya Nagi, Ryo Shimizu, Teruhisa Tsuchimoto and Mikiko Sodeoka

      Article first published online: 17 MAY 2011 | DOI: 10.1002/ejoc.201100453

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      Our trinary catalytic system, consisting of NiCl2/(R)-BINAP, Et3SiOTf, and amine base, allows asymmetric chlorination of aryl acetic acid derivatives in good yieldwith up to 89 % ee. Notably, γ-deprotonation and α-chlorination of an α,β-unsaturated compound also occurred with this system.

    3. Copper Catalysis

      Stereoselective Copper-Catalyzed Intramolecular Alkene Aminooxygenation: Effects of Substrate and Ligand Structure on Selectivity (pages 3679–3684)

      Monissa C. Paderes and Sherry R. Chemler

      Article first published online: 10 MAY 2011 | DOI: 10.1002/ejoc.201100444

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      A protocol for copper-catalyzed diastereoselective intramolecular alkene aminooxygenations is disclosed. Disubstituted pyrrolidines and five-membered cyclic ureas were synthesized in high yield and with high diastereoselectivity. Some success in a catalytic enantioselective desymmetrization reaction was realized. Selectivity can be tuned by substrate and catalyst structure.

    4. Tumor Vaccines

      Synthesis of Tn/T Antigen MUC1 Glycopeptide BSA Conjugates and Their Evaluation as Vaccines (pages 3685–3689)

      Hui Cai, Zhi-Hua Huang, Lei Shi, Peng Zou, Yu-Fen Zhao, Horst Kunz and Yan-Mei Li

      Article first published online: 2 MAY 2011 | DOI: 10.1002/ejoc.201100304

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      Tumor-associated MUC1 glycopeptides are attractive targets for antitumor immunotherapy. MUC1 glycopeptides containing the Tn and T antigen side chain were conjugated with bovine serum albumin. Thesevaccines were used for immunization of balb/c mice, and the immune responses were evaluated by enzyme-linked immunoabsorbent assay.

    5. Hypervalent Iodine

      Synthesis of a Range of Iodine(III) Compounds Directly from Iodoarenes (pages 3690–3694)

      Eleanor A. Merritt and Berit Olofsson

      Article first published online: 21 APR 2011 | DOI: 10.1002/ejoc.201100360

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      Herein we present the first direct synthetic routes to alkynyl(aryl)- and vinyl(aryl)iodonium tosylates from iodobenzene. The synthesis of several 1-substituted benziodoxolones from an iodine(I) precursor is also presented.

    6. Multicomponent Reactions

      A Practical, One-Pot Multicomponent Synthesis of α-Amidosulfides and Their Application as Latent N-Acylimines in the Friedel–Crafts Reaction (pages 3695–3699)

      Nicolas George, Mathieu Bekkaye, Géraldine Masson and Jieping Zhu

      Article first published online: 17 MAY 2011 | DOI: 10.1002/ejoc.201100426

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      Reaction of aldehydes, carbamates and phenylsulfinic acid afforded α-amidosulfones which were in situ converted into α-amidosulfides.

    7. Organocatalysis

      Enhanced Efficiency of Thiourea Catalysts by External Brønsted Acids in the Friedel–Crafts Alkylation of Indoles (pages 3700–3705)

      Eugenia Marqués-López, Ana Alcaine, Tomás Tejero and Raquel P. Herrera

      Article first published online: 7 JUN 2011 | DOI: 10.1002/ejoc.201100506

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      The use of thiourea catalysts with Brønsted acids renders the catalyst more effective in the enantioselective Friedel–Crafts reaction of indoles with nitroalkenes. Relative to the enantioselectivity observed with the thiourea catalyst alone, the final 3-substituted indole derivatives were synthesized with higher ee values as a result of cooperative effects between the catalyst and the acid additive.

    8. [3+2] Cycloadditions

      Silicon Lewis Acid Catalyzed [3+2] Cycloaddition Reactions of Hydrazones/Cyclopentadiene: Mild Access to Pyrazolidine Derivatives (pages 3706–3709)

      Alexandru Zamfir, Sebastian Schenker, Walter Bauer, Timothy Clark and Svetlana B. Tsogoeva

      Article first published online: 28 MAR 2011 | DOI: 10.1002/ejoc.201100206

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      A first catalytic metal-free approach to obtain synthetically and biologically important five-membered cyclic compounds by [3+2] cycloadditions of different N-acylhydrazones to cyclopentadiene has beendemonstrated. This reaction providespyrazolidines in excellent yields and high diastereoselectivities. DFT calculations explain the mechanism of the novel TMSOTf-catalyzed cycloaddition process.

    9. Bismuth(III) Triflate Catalysis

      Efficient Intramolecular Hydroarylation Catalysed by BiIII Triflate (pages 3710–3714)

      Bastien Cacciuttolo, Sophie Poulain-Martini and Elisabet Duñach

      Article first published online: 7 JUN 2011 | DOI: 10.1002/ejoc.201100213

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      Bismuth(III) trifluromethanesulfonate is an efficient and environmentally friendly catalyst for intramolecular hydroarylation, and it can be used at only 1 mol-%. No particular activation of the aromatic ring or of the olefin is needed for access to the tetralin and benzosuberan skeletons.

    10. Deproto-Metalation of Ferrocenes

      Diastereoselective Deprotonative Metalation of Sugar-Derived Ferrocene Esters Using Mixed Lithium–Cadmium Combinations (pages 3715–3718)

      Aare Sreeshailam, Gandrath Dayaker, Floris Chevallier, Thierry Roisnel, Palakodety Radha Krishna and Florence Mongin

      Article first published online: 4 APR 2011 | DOI: 10.1002/ejoc.201100264

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      (TMP)3CdLi allows efficient and chemoselective deprotonation reactions of ferrocene esters. Using derivatives synthesized fromα-D-glucofuranoses, diastereoselective reactions giving either the SP or the RP stereoisomer were performed.

    11. Gold-Catalyzed Cyclopropanation

      Gold(I)-Catalyzed Reactions of Propargyl Esters with Vinyl Derivatives (pages 3719–3722)

      Christian A. Sperger, Jørn E. Tungen and Anne Fiksdahl

      Article first published online: 3 MAY 2011 | DOI: 10.1002/ejoc.201100291

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      Gold(I)-catalyzed olefin cyclopropanations with propargyl esters and vinyl derivatives, directly connected to a heteroatom, efficiently provided highly substituted vinylcyclopropane derivatives in up to 99 % diastereoselectivity. The selective formation of trans-cyclopentenyl esters by a formal [3+2] cycloaddition is also reported, including a discussion on possible reaction pathways.

    12. Metallo–Organocatalysis

      Cooperative Copper(I) and Primary Amine Catalyzed Room-Temperature Carbocyclization of Formyl Alkynes (pages 3723–3727)

      Benjamin Montaignac, Maxime R. Vitale, Virginie Ratovelomanana-Vidal and Véronique Michelet

      Article first published online: 24 MAY 2011 | DOI: 10.1002/ejoc.201100464

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      Merging amino catalysis to the copper(I) activation of alkynes allowed the room temperature synthesis of a large variety of carbo- and heterocycles in good to excellent yields. Experimental results tend to demonstrate that the rate-determining step is the cyclization step and that it occurs according to a chair-like transition state.

    13. Asymmetric Organocatalysis

      Quinine-Catalysed Double Michael Addition of Malononitrile to 1,5-Disubstituted Pentadien-3-ones: A Stereoselective Route to Cyclohexanones (pages 3728–3731)

      Claudia De Fusco and Alessandra Lattanzi

      Article first published online: 26 APR 2011 | DOI: 10.1002/ejoc.201100282

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      Quinine-catalysed double Michael addition of dienones 1 with malononitrile affords cyclohexanones 2 in excellent diastereocontrol, moderate to good yields and good enantioselectivity. This simple noncovalentorganocatalytic cascade process represents an alternative route to enamine–iminium activation of enones to access compounds of type 2.

  10. Full Papers

    1. Top of page
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    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
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    11. Full Papers
    1. Rare Terpenoid Structure

      Dotofide, a Guanidine-Interrupted Terpenoid from the Marine Slug Doto pinnatifida (Gastropoda, Nudibranchia) (pages 3733–3737)

      Annika Putz, Stefan Kehraus, Guillermo Díaz-Agras, Heike Wägele and Gabriele M. König

      Article first published online: 28 APR 2011 | DOI: 10.1002/ejoc.201100347

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      Cladobranchia, a group of marine gastropods, do not have any kind of protective shell. According to some published investigations on this taxon, toxic secondary metabolites or cnidocysts (stinging cells) sequestered from the preferred cnidarian prey organisms are employed as alternative defence strategy. The unprecedented terpenoid dotofide derived from the cladobranch Doto pinnatifida was isolated.

    2. Chiral Discrimination

      NMR and Computational Investigations of the Chiral Discrimination Processes Involving a Cyclic Tetraamidic Chiral Selector (pages 3738–3747)

      Gloria Uccello-Barretta, Federica Balzano, Jonathan Martinelli, Francesco Gasparrini, Marco Pierini and Claudio Villani

      Article first published online: 1 JUN 2011 | DOI: 10.1002/ejoc.201100408

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      The host–guest systems 1/(R)-2 and 1/(S)-2 have been investigated by NMR spectroscopy and computational methods,revealing (a) the conformation of the host and the guest, (b) their relative stereochemistry in the diastereoisomeric solvates and (c) the complexation parameters of the two diastereoisomeric complexes.

    3. Hydrogenative Cyclization of Allenynes

      Experimental and Theoretical Investigation of Hydrogenative Cyclization of Allenynes (pages 3748–3754)

      Hyo-Tong Kim, Hyo-Sang Yoon, Woo-Young Jang, Youn K. Kang and Hye-Young Jang

      Article first published online: 12 MAY 2011 | DOI: 10.1002/ejoc.201100280

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      The platinum-catalyzed reductive cyclization of allenynes was conducted under hydrogenation conditions. Theoretical calculation results provide evidence that the catalytic cycle of this reaction begins with hydrometalation of the alkyne by a platinum–hydride complex.

    4. Cooperative Catalysis

      Cooperative Catalysis for the First Asymmetric Formal [3+2] Cycloaddition Reaction of Isocyanoacetates to α,β-Unsaturated Ketones (pages 3755–3760)

      Carlos Arróniz, Alberto Gil-González, Vladislav Semak, Carmen Escolano, Joan Bosch and Mercedes Amat

      Article first published online: 17 MAY 2011 | DOI: 10.1002/ejoc.201100409

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      Cooperation is the key: Cinchona alkaloid derived organocatalysts were combined with silver nitrate to achieve the firstasymmetric formal [3+2] cycloaddition reaction of isocyanoacetates to α,β-unsaturated ketones.

    5. Marine Natural Products

      New Structural Insights into Saraines A, B, and C, Macrocyclic Alkaloids from the Mediterranean Sponge Reniera (Haliclona) sarai (pages 3761–3767)

      Andrea Defant, Ines Mancini, Lucija Raspor, Graziano Guella, Tom Turk and Kristina Sepčić

      Article first published online: 13 JUN 2011 | DOI: 10.1002/ejoc.201100434

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      The strong proximity effect stabilizing the zwitterionic-like form in the amine aldehyde moiety of saraines A, B, and C has been investigated by NMR spectroscopy in different solvents, ESI mass spectrometry, peculiar chemical reactivity, and DFT calculations, giving good agreement with the Bürgi–Dunitz model.

    6. Iron Catalysis

      First Evidence of the Oxidative Addition of Fe0(N,N)2 to Aryl Halides: This Precondition Is Not a Guarantee of Efficient Iron-Catalysed C–N Cross-Coupling Reactions (pages 3768–3780)

      Guillaume Lefèvre, Marc Taillefer, Carlo Adamo, Ilaria Ciofini and Anny Jutand

      Article first published online: 17 JUN 2011 | DOI: 10.1002/ejoc.201100454

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      Electrogenerated Fe0(N,N)2 (N,N = phen, dmeda) undergo oxidative addition to aryl halides to form nucleophilic ArFeX(N,N)2, which do not react with N-nucleophiles even in the presence of a base. Fe0(N,N)2 cannot be generated in situ from precursors [Fe(acac)3] or FeCl3 due to a lack of reductants. This explains why they are inefficient precatalysts for C–N cross-coupling reactions.

    7. Natural Products

      New Potent Fluorescent Analogues of Strigolactones: Synthesis and Biological Activity in Parasitic Weed Germination and Fungal Branching (pages 3781–3793)

      Cristina Prandi, Ernesto G. Occhiato, Silvia Tabasso, Paola Bonfante, Mara Novero, Dina Scarpi, Maria Elena Bova and Ivana Miletto

      Article first published online: 28 JUN 2011 | DOI: 10.1002/ejoc.201100616

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      Strigolactones (SLs) are a new group of plant hormones that suppress lateral shoot branching and are crucial to root development; a role as signalling molecules in the rizosphere is well documented. In this work new fluorescent SLs analogues have been synthesized, spectroscopically investigated, and tested for bioactivity using seeds of Orobanche aegyptiaca and spores of Gigaspora margarita.

    8. Nucleosides

      Synthesis of Pyrimidine-Containing Nucleoside β-(R/S)-Hydroxyphosphonate Analogues (pages 3794–3802)

      Maïa Meurillon, Laurent Chaloin, Christian Périgaud and Suzanne Peyrottes

      Article first published online: 6 JUN 2011 | DOI: 10.1002/ejoc.201100219

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      The (R) and (S) diastereoisomers of nucleoside β-hydroxyphosphonate analogues in the uracil and cytosine series wereobtained from the reduction of a β-ketophosphonate intermediate.

    9. Natural Products

      Longeracemosones A–F, Aromatase Inhibitors from Dunbaria longeracemosa (pages 3803–3808)

      Vilailak Prachyawarakorn, Chulabhorn Mahidol and Somsak Ruchirawat

      Article first published online: 1 JUN 2011 | DOI: 10.1002/ejoc.201100410

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      Six new dihydroflavonols and two known flavonoids have been isolated from Dunbaria longeracemosa. The absolute configurations of the isolated compounds were determined by analysis of the CD spectra and by the modified Mosher's method. Three of the compounds exhibit potent aromatase inhibitory activity with IC50 values of 0.3, 0.4,and 1.2 μM, respectively.

    10. Cancer Chemopreventive Agents

      Protoberberine Alkaloids and Cancer Chemopreventive Properties of Compounds from Alangium salviifolium (pages 3809–3814)

      Phanruethai Pailee, Vilailak Prachyawarakorn, Chulabhorn Mahidol, Somsak Ruchirawat and Prasat Kittakoop

      Article first published online: 9 JUN 2011 | DOI: 10.1002/ejoc.201100423

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      Protoberberine alkaloids 1 and 2, triterpene caffeate 3, and β-D-glucopyranos-1-yl N-methylpyrrole-2-carboxylate (5) have been isolated from Alangium salviifolium. Radical scavenging, antioxidant, and aromatase inhibitory activities imply that the isolated compounds might be useful for cancer chemoprevention.

    11. [2+2+2] Cycloadditions

      Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides (pages 3815–3824)

      Ryan M. Stolley, Michael T. Maczka and Janis Louie

      Article first published online: 24 MAY 2011 | DOI: 10.1002/ejoc.201100428

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      The nickel-catalyzed [2+2+2] cycloaddition reactions of diynes and cyanamides have been explored. The catalytic system is tolerant of a variety of cyanamides, regioselective, and can catalyze a three-component reaction, all in good to excellent yields.

    12. Trifluorohexosides

      De Novo Synthesis of Racemic 4-Deoxy-4,4-difluoro- and 2,4-Dideoxy-2,4,4-trifluorohexosides (pages 3825–3836)

      Guy T. Giuffredi, Bruno Bernet and Véronique Gouverneur

      Article first published online: 17 JUN 2011 | DOI: 10.1002/ejoc.201100565

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      A range of different racemic 4-deoxy-4,4-difluoro- and 2,4-dideoxy-2,4,4-trifluorohexosides was prepared from three commercially available two-carbon building blocks in overall yields of up to 28 %.

    13. 1,3,5-Trisubstituted Pyrazoles

      Facile Access to 3,5-Dihalogenated Pyrazoles by Sydnone Cycloaddition and their Versatile Functionalization by Pd-Catalyzed Cross-Coupling Processes (pages 3837–3848)

      Thierry Delaunay, Mazen Es-Sayed, Jean-Pierre Vors, Nuno Monteiro and Geneviève Balme

      Article first published online: 16 MAR 2011 | DOI: 10.1002/ejoc.201100119

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      3-Bromo-5-iodopyrazoles, readily accessible by 1,3-dipolar cycloaddition of 4-halosydnones with 1-halopropiolates and subsequent dealkoxycarbonylation, are valuable scaffolds for the versatile functionalization of the pyrazole ring by Pd-catalyzed cross-coupling reactions.

    14. Helicene Phosphites

      Helicene-Based Phosphite Ligands in Asymmetric Transition-Metal Catalysis: Exploring Rh-Catalyzed Hydroformylation and Ir-Catalyzed Allylic Amination (pages 3849–3857)

      Zuzana Krausová, Petr Sehnal, Bojan P. Bondzic, Serghei Chercheja, Peter Eilbracht, Irena G. Stará, David Šaman and Ivo Starý

      Article first published online: 12 MAY 2011 | DOI: 10.1002/ejoc.201100259

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      Helically chiral phosphites derived from the [6]helicene-like scaffold were prepared and applied to RhI-catalyzed hydroformylation of terminal alkenes and IrI-catalyzed allylic amination. Excellent regioselectivity in favor of the branched products was observed along with moderate (for hydroformylation) or high (for amination) enantioselectivity.

    15. Heterocyclic Chemistry

      Stereocontrolled Generation of Benzo[a]- and Indolo[2,3-a]quinolizidines from (S)-Tryptophanol and (S)-(3,4-Dimethoxyphenyl)alaninol-Derived Lactams (pages 3858–3863)

      Maria Pérez, Federica Arioli, Gianna Rigacci, Maria M. M. Santos, Arantxa Gómez-Esqué, Carmen Escolano, Pedro Florindo, Carlos Ramos, Joan Bosch and Mercedes Amat

      Article first published online: 12 MAY 2011 | DOI: 10.1002/ejoc.201100294

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      Diastereodivergent access to indolo[2,3-a]quinolizidines from an (S)-tryptophanol-derived lactam using either HCl or BF3·Et2O/KOH is reported. An intermediate oxazolinium salt is formed under the latter conditions. Similar Pictet–Spengler cyclizations from (S)-(3,4-dimethoxyphenyl)alaninol lead to trans-H-6/H-11b benzo[a]quinolizidines regardless of the cyclization agent used.

    16. Diastereoselective Synthesis

      Stereoselective Synthesis of 2H-Chromans by Reductive Deoxygenation of Differently Substituted 2-Sulfinylmethylchroman-2-ols (pages 3864–3877)

      Gloria Hernández-Torres, M. Carmen Carreño, Antonio Urbano and Françoise Colobert

      Article first published online: 17 JUN 2011 | DOI: 10.1002/ejoc.201100436

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      A two-step diastereoselective access to 2H-chromans is reported from dihydrocoumarins and methyl sulfoxides. Good-to-excellent diastereoselectivities were achieved in the key reductive deoxygenation step, depending on the type of substitution both on the sulfoxide and on the dihydrobenzopyran core.

    17. Fluorous Glycopeptide Antigens

      Synthesis and Antibody Binding of Highly Fluorinated Amphiphilic MUC1 Glycopeptide Antigens (pages 3878–3887)

      Tobias Platen, Timo Schüler, Wolfgang Tremel and Anja Hoffmann-Röder

      Article first published online: 21 JUN 2011 | DOI: 10.1002/ejoc.201100648

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      Functional fluorous mucin-type antigens have been prepared in which double-tailed hydrocarbon/fluorocarbon lysine derivatives are conjugated to a tumor-associated TN building block and a full 20 amino acid tandem repeat sequence of the glycopeptide mucin-1. The latter specifically binds to various anti-MUC1 mouse antibodies.

    18. [2+2] Photocycloadditions

      [2+2] Photocycloaddition of Symmetrically Disubstituted Alkenes to 2(5H)-Furanones: Diastereoselective Entry to 1,2,3,4-Tetrasubstituted Cyclobutanes (pages 3888–3895)

      Sònia Parés, Pedro de March, Josep Font, Ramon Alibés and Marta Figueredo

      Article first published online: 6 MAY 2011 | DOI: 10.1002/ejoc.201100067

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      The photochemical [2+2] cycloaddition of 2(5H)-furanones to symmetrical 1,4-difunctionalized 2-butenes has been studied. The use of the chiral lactone 11 as the starting substrate enables stereoselective access to densely functionalized 1,2,3,4-tetrasubstituted cyclobutanes.

    19. Multicomponent Reactions

      Catalyst-Free Strecker Reaction in Water: A Simple and Efficient Protocol Using Acetone Cyanohydrin as Cyanide Source (pages 3896–3903)

      Paola Galletti, Matteo Pori and Daria Giacomini

      Article first published online: 5 APR 2011 | DOI: 10.1002/ejoc.201100089

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      An efficient application of acetone cyanohydrin in water for a multicomponent synthesis of α-amino nitriles is described.

    20. Gold Catalysis

      AuI-Catalyzed Intramolecular Cyclization of 2-Alkenylphenyl Carbonyl Compounds: Exploring the Oxophilic Lewis Acidity of AuI Species (pages 3904–3910)

      Arun R. Jagdale and So Won Youn

      Article first published online: 22 MAR 2011 | DOI: 10.1002/ejoc.201100113

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      AuI-catalyzed intramolecular cyclization of 2-alkenylphenyl carbonyl compounds to afford a variety of indene, indenol, and indanone ring systems was developed. AuI activates the carbonyl group of β-keto esters, aldehydes, and ketones and exhibits oxophilicity in the presence of C–C multiple bonds. β-Keto esters could also participate as the electrophile in reactions with carbon nucleophiles.

    21. Nonnatural Glycopeptides

      Synthesis of α-N-Linked Glycopeptides (pages 3911–3919)

      Cinzia Colombo and Anna Bernardi

      Article first published online: 3 MAY 2011 | DOI: 10.1002/ejoc.201100124

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      Neo-glycopeptides featuring the unnatural α-N-glycosyl linkage can now be synthesized in solution and in the solid phase by using the building blocks and methodologies described in this paper.

    22. Farnesyltransferase Inhibition

      SNAr and Palladium-Catalyzed Reactions of Deactivated Thiophene: Application to the Synthesis of Protein Farnesyltransferase Inhibitors (pages 3920–3931)

      Sébastien Lethu and Joëlle Dubois

      Article first published online: 13 MAY 2011 | DOI: 10.1002/ejoc.201100215

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      A small library of 3-(4-chlorophenyl)-4-cyanothiophene-2-carboxylic acids derived from a hit compound was designed using SNAr and palladium-catalyzed reactions for structure-activity relationship studieson protein farnesyltransferase. Some library members efficiently inhibited farnesyltransferase with IC50s around or below 100 nM.

    23. Chiral BINOL–Phosphoric Acids

      A Protecting-Group-Free Route to Chiral BINOL–Phosphoric Acids (pages 3932–3937)

      Baojian Li and Pauline Chiu

      Article first published online: 20 MAY 2011 | DOI: 10.1002/ejoc.201100328

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      A two-step, protecting-group-free route for the synthesis of 3,3′-disubstituted and 6,6′-disubstituted chiral BINOL–phosphoric acids has been realized. Starting from commercially available brominated BINOLs, esterification followed by direct Suzuki coupling yields the desired products.

    24. Synthesis of Spiroketals

      A Flexible Approach to 6,5-Benzannulated Spiroketals (pages 3938–3945)

      Zoe E. Wilson, Jonathan G. Hubert and Margaret A. Brimble

      Article first published online: 18 MAY 2011 | DOI: 10.1002/ejoc.201100345

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      Substituted 6,5-benzannulated spiroketals were readily produced by Horner–Wadsworth–Emmons olefination and a one-pot hydrogenation/deprotection/cyclisation process.

    25. Enzyme Catalysis

      Enzymatic Total Synthesis of Banana Volatile (S)-2-Pentyl (R)-3-Hydroxyhexanoate (pages 3946–3950)

      Maria Kallergi, Dimitris Kalaitzakis and Ioulia Smonou

      Article first published online: 10 JUN 2011 | DOI: 10.1002/ejoc.201100368

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      The first enzymatic synthesis of banana volatile (S)-2-pentyl (R)-3-hydroxyhexanoate in 79 % yield and high optical purity is presented. The high enantiopurity wasintroduced by two enzymatic reductions in the presence of ketoreductases and an enzymatic transesterification in the presence of Candida antarctica lipase B.

    26. One-Pot Carboboration

      One-Pot Carboboration of Alkynes Using Lithium Borylcyanocuprate and the Subsequent Suzuki–Miyaura Cross-Coupling of the Resulting Tetrasubstituted Alkenylborane (pages 3951–3958)

      Yuri Okuno, Makoto Yamashita and Kyoko Nozaki

      Article first published online: 17 MAY 2011 | DOI: 10.1002/ejoc.201100373

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      One-pot carboboration of internal alkynes was achieved by using lithium borylcyanocupurate and allyl bromide. After exchange of the diamine ligand on the boron centerto pinacolate, the obtained pinacol ester was subjected to Suzuki–Miyaura cross-coupling to give the all-carbon-substituted alkene.

    27. Radiation Stability of an Extractant

      Hydrolysis and Radiation Stability of m-Xylylene Bis-diglycolamide: Synthesis and Quantitative Study of Degradation Products by HPLC–APCI+ (pages 3959–3969)

      Hitos Galán, María Teresa Murillo, Rosa Sedano, Ana Núñez, Javier de Mendoza, Amparo González-Espartero and Pilar Prados

      Article first published online: 27 JUN 2011 | DOI: 10.1002/ejoc.201100443

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      Compound 1, an extractant of AmIII and EuIII from nuclear waste, was irradiated with γ irradiation at 1000 kGy with external 60Co sources, resulting in 17 subproducts. These compounds were synthesized and qualitative and quantitative analyses of irradiated 1 were performed. Two of the major degradation products were stable to radiation and showed high D values for AmIII and EuIII extraction.

    28. Chlorins and Bacteriochlorins

      [8π+2π] Cycloaddition of meso-Tetra- and 5,15-Diarylporphyrins: Synthesis and Photophysical Characterization of Stable Chlorins and Bacteriochlorins (pages 3970–3979)

      Nelson A. M. Pereira, Sofia M. Fonseca, Arménio C. Serra, Teresa M. V. D. Pinho e Melo and Hugh D. Burrows

      Article first published online: 1 JUN 2011 | DOI: 10.1002/ejoc.201100465

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      4,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-fused chlorins and bacteriochlorins obtained through [8π+2π] cycloaddition of diazafulvenium methides with tetrapyrrolic macrocycles showed potential for various biomedical applications.

    29. Asymmetric Catalysis

      Opposite Enantiomers from Minor Enantiomer Recycling and Dynamic Kinetic Resolution Using a Single Biocatalyst (pages 3980–3984)

      Anna Laurell and Christina Moberg

      Article first published online: 24 MAY 2011 | DOI: 10.1002/ejoc.201100467

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      The (R) enantiomer of the O-acetylated cyanohydrin from (E)-2-butenal was obtained by minor enantiomer recycling, whereas the (S) enantiomer of the same product was obtained by dynamic kinetic resolution with the use of the same catalyst.

    30. C–F Activation

      Exploration of the Scope of Pt-Catalyzed C–F Activation (pages 3985–3994)

      Lauren Keyes, Alex D. Sun and Jennifer A. Love

      Article first published online: 7 JUN 2011 | DOI: 10.1002/ejoc.201100478

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      The scope of directing groups in Pt-catalyzed cross-coupling of polyfluoroarenes is described. Both methylation and methoxylation is presenting, including a one-pot method for sequential C–C and C–O bond formation.

    31. Trehalase Inhibitors

      Synthesis of Novel Iminosugar-Based Trehalase Inhibitors by Cross-Metathesis Reactions (pages 3995–4000)

      Davide Bini, Matilde Forcella, Laura Cipolla, Paola Fusi, Camilla Matassini and Francesca Cardona

      Article first published online: 1 JUN 2011 | DOI: 10.1002/ejoc.201100484

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      Several iminosugar-based trehalase inhibitors were synthesized by homo- and heterodimerization mediated by Grubbs Ru–carbene-catalyzed cross-metathesis reactions. Preliminary biological evaluation ofthe synthesized compounds for their inhibitory activity against commercially available porcine trehalase showed nojirimycin dimer as the most active compound, possessing a Ki value of 44 μM.

    32. Thieno-fused Heterocycles

      A Novel Radical Cyclization Approach to Thieno-Fused Heterocycles (pages 4001–4007)

      Prabal P. Singh, Ashok K. Yadav, Hiriyakkanavar Ila and Hiriyakkanavar Junjappa

      Article first published online: 27 MAY 2011 | DOI: 10.1002/ejoc.201100516

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      An efficient synthesis of novel aryl/heteroaryl-substituted thieno-fused heterocycles, that is, thieno[2,3-b]thiophenes, thieno[2,3-b]indoles, and pyrazolo[3,2-c]thiophenes, involving radical-mediated cyclization of2-(2-bromoheteroaryl)-3-methylthio-3-aryl/heteroaryl acrylonitriles is reported.

    33. Azasugars

      Stereoselective Strecker and Carbamate Annulation Methodology for the Synthesis of 1-Amino-1,2,5-trideoxy-2,5-imino-L-iditol (pages 4008–4014)

      Anna L. Win-Mason, Emma M. Dangerfield, Peter C. Tyler, Bridget L. Stocker and Mattie S. M. Timmer

      Article first published online: 1 JUN 2011 | DOI: 10.1002/ejoc.201100523

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      A highly stereoselective and efficient synthesis of L-ido-aminoiminohexitol is presented. Key steps include a stereoselective Strecker reaction and the extension of our carbamate annulation methodology that allows for the cyclization of protected and functionalized alkenylamines. Insight into the mechanism of the carbamate annulation is also provided.

    34. Enantioselective C=C Bioreduction

      Biocatalyzed Enantioselective Reduction of Activated C=C Bonds: Synthesis of Enantiomerically Enriched α-Halo-β-arylpropionic Acids (pages 4015–4022)

      Elisabetta Brenna, Francesco G. Gatti, Alessia Manfredi, Daniela Monti and Fabio Parmeggiani

      Article first published online: 17 JUN 2011 | DOI: 10.1002/ejoc.201100537

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      The enantioselective biocatalyzed reduction of the C=C bond of methyl α-halo-β-arylacrylates was investigated by meansof baker's yeast fermentation and OYE1–3 biotransformations.

    35. Selective Sialylation

      C-5 Modified S-Benzoxazolyl Sialyl Donors: Towards More Efficient Selective Sialylations (pages 4023–4027)

      Benjamin N. Harris, Payal P. Patel, Chase P. Gobble, Matthew J. Stark and Cristina De Meo

      Article first published online: 8 JUN 2011 | DOI: 10.1002/ejoc.201100539

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      Almost complete stereoselectivity was achieved in the selective glycosylation of C-5 modified S-benzoxazolyl sialyl donor 1d and thioethyl galactosyl acceptor 2 uponactivation with bismuth triflate in the presence of dichloromethane/tetrahydrofuran (1:1) as solvent.

    36. Organocatalysis

      Organocatalyzed Synthesis of Tertiary α-Hydroxyphosphonates by a Highly Regioselective Modified Pudovik Reaction (pages 4028–4036)

      Maria Teresa Barros and Ana Maria Faísca Phillips

      Article first published online: 9 MAY 2011 | DOI: 10.1002/ejoc.201100308

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      Quinine was used to catalyze a modified Pudovik reaction between α-haloketones and dialkyl phosphites. A variety of tertiary α-hydroxyphosphonates was obtained in a reaction that was highly regioselective even with aromatic α-haloketones.

    37. Stereoselective Grignard Additions

      Stereoselective Addition of Grignard Reagents to New P-Chirogenic N-Phosphinoylbenzaldimines: Effect of the Phosphorus Substituents on the Stereoselectivity (pages 4037–4045)

      Irene Notar Francesco, Coraline Egloff, Alain Wagner and Françoise Colobert

      Article first published online: 8 JUN 2011 | DOI: 10.1002/ejoc.201100380

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      The addition of Grignard reagents to various P-chirogenic [(diaryl- and (alkyl)(aryl)phosphinoyl]imines provides a stereoselective method for the synthesis of chiralphosphinoylamines. The reaction tolerates a wide range of Grignard reagents and affords the corresponding adducts in excellent yields and with good stereoselectivities.

    38. Asymmetric Organocatalysis

      Organocatalyzed Aziridination of α-Branched Enals: Enantioselective Synthesis of Aziridines with a Quaternary Stereo­center (pages 4046–4052)

      Alaric Desmarchelier, Danilo Pereira de Sant'Ana, Vincent Terrasson, Jean Marc Campagne, Xavier Moreau, Christine Greck and Renata Marcia de Figueiredo

      Article first published online: 1 JUN 2011 | DOI: 10.1002/ejoc.201100437

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      Enantioselective aziridination of α-substituted α,β-unsaturated aldehydes is reported. The transformation is driven by diarylprolinol trimethylsilyl ether. A varietyof N-tosylaziridine bearing a chiral quaternary stereocenter at the α-position of the aldehydes was obtained.

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