European Journal of Organic Chemistry

Cover image for Vol. 2009 Issue 22

August 2009

Volume 2009, Issue 22

Pages 3651–3809

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Retraction
    1. Synthesis and Hormonal Activity of the (25S)-Cholesten-26-oic Acids – Potent Ligands for the DAF-12 Receptor in Caenorhabditis elegans (Eur. J. Org. Chem. 22/2009) (page 3651)

      René Martin, Eugeni V. Entchev, Frank Däbritz, Teymuras V. Kurzchalia and Hans-Joachim Knölker

      Version of Record online: 14 JUL 2009 | DOI: 10.1002/ejoc.200990060

  2. Graphical Abstract

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

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

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

      Catalytic Enantioselective Aldol Additions to Ketones (pages 3661–3671)

      Shinya Adachi and Toshiro Harada

      Version of Record online: 13 MAY 2009 | DOI: 10.1002/ejoc.200900166

      Thumbnail image of graphical abstract

      This microreview presents an overview of progresses in catalytic enantioselective aldol addition to ketones. The reaction, once thought to be challenging owing to the lower reactivity and the decreased stericdiscrimination of a ketone carbonyl group, has been realized recently based on the activation of acceptor ketones and/or nucleophile enolates.

  5. Short Communications

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

      Fluorescent Cyclohexyl-Based Chemosensors for Selective Sensing of TMA Malonate in DMSO/Water (pages 3673–3677)

      Ana M. Costero, Josep V. Colomer, Salvador Gil and Margarita Parra

      Version of Record online: 22 JUN 2009 | DOI: 10.1002/ejoc.200900383

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      A new cyclohexyl-based fluorescent system is able to recognize trimethylammonium (TMA) malonate through the inhibition of FRET in buffered DMSO/water solutions. Longer and shorter homologous dicarboxylates did not give rise to changes in the solution fluorescent properties.

    2. Stereocontrolled Transformations

      Short and Stereoselective Total Synthesis of Δ-11,13-Didehydroguaianes and -guaianolides: Synthesis of (±)-Achalensolide and (±)-Pechueloic Acid; Revision of the Structure of (+)-Rupestonic Acid (pages 3678–3682)

      Thomas Sainte-Luce Banchelin, Sébastien Carret, Audrey Giannini and Jean-Pierre Deprés

      Version of Record online: 19 JUN 2009 | DOI: 10.1002/ejoc.200900456

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      The total synthesis of pechueloic acid (1) as well as the first syntheses of rupestonic acid (3) and achalensolide (5) were achieved in nine regio- and stereocontrolled steps, via hydroazulenone 6 (a versatile intermediate), through efficient C-1 epimerization, selective C-8,9 hydrogenation and stereocontrolled 1,6-conjugate addition of an acrylate equivalent.

    3. Catalytic Reduction of Ketimines

      1,1′-Binaphthyldiamine-Based Lewis Bases as Readily Available and Efficient Organocatalysts for the Reduction of N-Aryl and N-Alkyl Ketimines (pages 3683–3687)

      Stefania Guizzetti, Maurizio Benaglia and Giuseppe Celentano

      Version of Record online: 24 JUN 2009 | DOI: 10.1002/ejoc.200900524

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      An organocatalyst, easily prepared in a single step by condensation of picolinic acid and readily available 1,1′-binaphthyldiamine, promoted the synthesis of chiral secondary and primary amines in highyield and stereoselectivity. These catalysts are able to promote the reduction not only of N-aryl but also of N-alkyl and N-benzyl ketimines, often in quantitative yields and up to 87 % enantioselectivity.

    4. Suzuki–Miyaura Cross-Coupling

      A General and Efficient Suzuki–Miyaura Cross-Coupling Protocol Using Weak Base and No Water: The Essential Role of Acetate (pages 3688–3692)

      Bing Wang, Hui-Xia Sun and Zhi-Hua Sun

      Version of Record online: 22 JUN 2009 | DOI: 10.1002/ejoc.200900538

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      CsOAc promotes Suzuki–Miyaura cross-coupling and related Pd-catalyzed reactions under anhydrous conditions as effectively as stronger bases. A neglected six-membered transition-state model was proposed to give alternative insight into the key process of transmetalation.

    5. Chiral Brønsted Acids

      BINBAM – A New Motif for Strong and Chiral Brønsted Acids (pages 3693–3697)

      Marcel Treskow, Jörg Neudörfl and Ralf Giernoth

      Version of Record online: 17 JUN 2009 | DOI: 10.1002/ejoc.200900548

      Thumbnail image of graphical abstract

      BINBAM [(R)-1,1′-binaphthyl-2,2′-bis(sulfon)amide] is the first member of a new generation of chiral Brønsted acids. It is easily accessible from commercially available BINOL and its 3,3′-derivatives. It shows higher Brønsted acidity than competing phosphoric acid derivatives like the TRIP family.

    6. C–H Arylation

      Switching the Regioselectivity of Direct C–H Arylation of 1,3-Dimethyluracil (pages 3698–3701)

      Miroslava Čerňová, Radek Pohl and Michal Hocek

      Version of Record online: 24 JUN 2009 | DOI: 10.1002/ejoc.200900586

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      Direct C–H arylation of pyrimidine nucleobase proceeds regioselectively, and the selectivity (and mechanism) can be efficiently switched by copper iodide. In the absenceof CuI, the arylations of 1,3-dimethyluracil lead to 5-aryluracils, while in the presence of CuI, to 6-aryl derivatives.

  6. Full Papers

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

      Synthesis and Hormonal Activity of the (25S)-Cholesten-26-oic Acids – Potent Ligands for the DAF-12 Receptor in Caenorhabditis elegans (pages 3703–3714)

      René Martin, Eugeni V. Entchev, Frank Däbritz, Teymuras V. Kurzchalia and Hans-Joachim Knölker

      Version of Record online: 10 JUN 2009 | DOI: 10.1002/ejoc.200900443

      Thumbnail image of graphical abstract

      An elegant synthetic approach to the (25S)-cholesten-26-oic acids has been developed using a stereoselective Evans aldol reaction as key-step. These steroids are potent ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans. Our biological studies confirm (25S)-Δ7-dafachronic acid (1) as the most active ligand known so far.

    2. Porphyrin Chemistry

      Formyl-Porphyrin and Formyl-Fullerenoporphyrin Building Blocks for the Construction of Multiporphyrin Arrays (pages 3715–3725)

      Maxence Urbani, Julien Iehl, Iwona Osinska, Rémy Louis, Michel Holler and Jean-François Nierengarten

      Version of Record online: 27 MAY 2009 | DOI: 10.1002/ejoc.200900358

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      A formyl-fullerenoporphyrin building block has been prepared and used for the construction of a pentaporphyrin derivative surrounded by four peripheral C60units. By following a similar strategy, a nonaporphyrin array was prepared from a bis-porphyrin building block bearing an aldehyde function.

    3. Heterocyclic Chemistry

      Synthesis of Enantiopure 2-Aryl(Alkyl)-2-trifluoromethyl-Substituted Morpholines and Oxazepanes (pages 3726–3731)

      Jean Nonnenmacher, Fabienne Grellepois and Charles Portella

      Version of Record online: 24 JUN 2009 | DOI: 10.1002/ejoc.200900387

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      Novel enantiopure morpholines and oxazepanes containing a quaternary trifluoromethyl substituent have been preparedfrom a common O-allyl amino ether intermediate by a 6-exo or 7-endo nucleophilic cyclisation process.

    4. γ-Halocarbanion Chemistry

      Reactions of Carbanions of 1-Chloro-5-(phenylsulfonyl)pent-2-enes: Synthesis of Vinyl-Substituted Tetrahydrofurans (pages 3732–3740)

      Anna Wojtasiewicz, Bartosz Lewandowski, Marek Judka and Mieczysław Mąkosza

      Version of Record online: 17 JUN 2009 | DOI: 10.1002/ejoc.200900275

      Thumbnail image of graphical abstract

      Carbanions of 1-chloro-5-(phenylsulfonyl)pent-2-enes can be considered as vinylogues of γ-halocarbanions. They undergo intramolecular SN2′ 1,3-substitution and 1,5-elimination to produce 2-(phenylsulfonyl)-1-vinylcyclopropanes and 1-(phenylsulfonyl)penta-2,4-dienes. They also add rapidly to aromatic aldehydes to produce the corresponding 2-aryl-3-(phenylsulfonyl)-5-vinyltetrahydrofurans.

    5. Metathesis of Chiral Enehydrazides

      First Asymmetric Synthesis of (Un)saturated 1-Alkylbenzo[c]azepin-3-ones: Extension to the Corresponding Benzazepines (pages 3741–3752)

      David Dumoulin, Stéphane Lebrun, Eric Deniau, Axel Couture and Pierre Grandclaudon

      Version of Record online: 16 JUN 2009 | DOI: 10.1002/ejoc.200900365

      Thumbnail image of graphical abstract

      A flexible asymmetric synthesis of chiral (1R)-1-alkylated benzazepinone and benzazepine derivatives that combines a highly stereoselective 1,2-addition to SAMP-hydrazones with the ring-closing metathesis of styrenic enehydrazides has been achieved.

    6. Heterocyclic Chemistry

      Efficient and Selective Method for the Synthesis of Dihydrodipyridopyrazines Based on the Pd-Catalysed Amination of Halopyridines (pages 3753–3764)

      Oana-Irina Patriciu, Adriana-Luminiţa Fînaru, Stéphane Massip, Jean-Michel Léger, Christian Jarry and Gérald Guillaumet

      Version of Record online: 16 JUN 2009 | DOI: 10.1002/ejoc.200900404

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      Specific syntheses of each of the unsymmetrically substituted dihydrodipyridopyrazine isomers A and B have been completed. The novel strategy that was developed for their syntheses featured Pd catalysis for key couplings, followed by a substitution/reduction/cyclization/substitutionsequence of suitable nitro-substituted N,N′-dipyridinylamine products.

    7. Cyclopropylboronic Esters

      Enantiomerically Pure Vinylcyclopropylboronic Esters (pages 3765–3782)

      Erwin Hohn, Jiří Paleček, Jörg Pietruszka and Wolfgang Frey

      Version of Record online: 17 JUN 2009 | DOI: 10.1002/ejoc.200900414

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      Isomerically pure vinylcyclopropanes (e.g., 10) have been prepared from cyclopropylboronic esters (e.g., 3). A number of alternative procedures for their synthesis via the corresponding alkyltrifluoroborateshave been established and they require relatively mild reaction conditions for their activation. The sequence has been applied to the synthesis of natural dictypterene A (38).

    8. Staudinger-Ligated Glycoconjugates

      Utilizing Staudinger Ligation for the Synthesis of Glycoamino Acid Building Blocks and Other Glycomimetics (pages 3783–3789)

      Alexander Schierholt, Harun A. Shaikh, Jörn Schmidt-Lassen and Thisbe K. Lindhorst

      Version of Record online: 22 JUN 2009 | DOI: 10.1002/ejoc.200900437

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      Staudinger ligation can be utilized in the synthesis of multivalent glycomimetics such as glycoclusters and glycoamino acid building blocks.

    9. Chiral Propargylamines

      Asymmetric Addition of Terminal Alkynes to N-(Diphenylphosphinoyl)imines Promoted by Stoichiometric Amounts of a Proline-Derived β-Amino Alcohol (pages 3790–3794)

      Wenjin Yan, Bin Mao, Shaoqun Zhu, Xianxing Jiang, Zhongli Liu and Rui Wang

      Version of Record online: 19 JUN 2009 | DOI: 10.1002/ejoc.200900342

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      The highly enantioselective alkynylation of N-(diphenylphosphinoyl)imines has beenachieved by the use of a proline-derived β-amino alcohol and diethylzinc.

    10. Supported Mercaptoacetic Acid

      Deprotection of N-Nosyl-α-amino Acids by Using Solid-Supported Mercaptoacetic Acid (pages 3795–3800)

      Rosaria De Marco, Maria Luisa Di Gioia, Antonella Leggio, Angelo Liguori and Maria Caterina Viscomi

      Version of Record online: 19 JUN 2009 | DOI: 10.1002/ejoc.200900271

      Thumbnail image of graphical abstract

      A solid-supported thiol has been conveniently prepared by treating an S-protected mercaptoacetic acid with Wang resin. Deprotection of the thiol function provided the supported nucleophile, which was used to remove the nosyl group from the α-amino function of nosyl-α-amino acids in a polymer-assisted solution-phase reaction.

    11. Multicomponent Reactions

      The Passerini Reaction with CF3-Carbonyl Compounds – Multicomponent Approach to Trifluoromethyl Depsipeptides (pages 3801–3808)

      Anton V. Gulevich, Inga V. Shpilevaya and Valentine G. Nenajdenko

      Version of Record online: 17 JUN 2009 | DOI: 10.1002/ejoc.200900330

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      The first detailed investigation of the Passerini reaction with CF3-carbonyl compounds is reported. The reaction providesa new approach to trifluorolactic acid derivatives and CF3-substituted depsipeptides.

  7. Retraction

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