European Journal of Organic Chemistry

Cover image for Vol. 2013 Issue 7

March 2013

Volume 2013, Issue 7

Pages 1179–1376

  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
      Effective and Versatile Strategy for the Total Solid-Phase Synthesis of Alkanethiols for Biological Applications (Eur. J. Org. Chem. 7/2013)

      Elisabet Prats-Alfonso, Sabine Oberhansl, Anna Lagunas, Elena Martínez, Josep Samitier and Fernando Albericio

      Article first published online: 20 FEB 2013 | DOI: 10.1002/ejoc.201390015

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      The cover picture shows the comparison between the fashion designs made with tailored fabrics and the solid-phase synthetic platform we propose. The similarity arises from the capacity of the synthetic platform to perform the customized design of the alkyl thiols made to your convenience like the patterns made by a tailor for a specific customer. The background of the picture simulates the texture of a fabric to enhance this comparison. Details are discussed in the article by F. Albericio et al. on p. 1233 ff.

  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. 7/2013 (pages 1179–1185)

      Article first published online: 20 FEB 2013 | DOI: 10.1002/ejoc.201390017

  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. Cyclization

      Prins-Type Cyclization Reactions in Natural Product Synthesis (pages 1193–1208)

      Xun Han, GuangRong Peh and Paul E. Floreancig

      Article first published online: 6 FEB 2013 | DOI: 10.1002/ejoc.201201557

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      Tetrahydropyrans are subunits in a wide range of biologically active natural products. Prins-type cyclization reactions, in which a π-nucleophile adds to an appended oxocarbenium ion, are effective for constructing these rings. This microreview covers variations of this reaction that have been applied to natural product synthesis with a focus on the method of oxocarbenium ion formation and type of π-nucleophile.

  5. Short Communications

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

      Synthesis of a Pillar[5]arene-Based Heteroditopic Host and Its Complexation with n-Octyltriethylammonium Salts (pages 1209–1213)

      Lingyan Gao, Shengyi Dong, Bo Zheng and Feihe Huang

      Article first published online: 25 JAN 2013 | DOI: 10.1002/ejoc.201201590

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      A pillar[5]arene-based heteroditopic receptor containing an anion recognition site promotes the binding affinity to n-octyltriethylammonium salts in chloroform, whereas the corresponding monotopic host shows weak binding abilities with these guests. The urea group and the macrocyclic unit not only provide positioned binding sites but also induced positive cooperative effects for contact ion pairs.

    2. Radiolabeling

      11C Click Chemistry Using [11C]Methyl Azide: Simplified, Versatile, and Practical Alternative Access to [11C]Nucleosides and [11C]Oligonucleotides for PET Imaging (pages 1214–1217)

      Thomas Bordenave, Puja Panwar Hazari, Damien James, Anil K. Mishra, Magali Szlosek-Pinaud and Eric Fouquet

      Article first published online: 24 JAN 2013 | DOI: 10.1002/ejoc.201201379

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      Click chemistry in its “hot” version: A one-step approach to nucleosides opens the way to the development of a new class of positron emission tomography (PET) tracers.

    3. Oxidative Amidation

      Copper-Catalyzed Oxidative Coupling of Carboxylic Acids with N,N-Dialkylformamides: An Approach to the Synthesis of Amides (pages 1218–1222)

      P. Santhosh Kumar, G. Sathish Kumar, R. Arun Kumar, N. Veera Reddy and K. Rajender Reddy

      Article first published online: 24 JAN 2013 | DOI: 10.1002/ejoc.201201544

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      A new synthetic approach to amide bond formation through the oxidative coupling of N,N-dialkylformamides with carboxylic acids was achieved by using a copper catalyst and aqueous tert-butyl hydroperoxide (TBHP) as a sacrificial oxidant. Furthermore, this method was applied in the coupling of chiral amino acids in which the stereochemistry was retained in the resulting amide products.

      Corrected by:

      Correction: Copper-Catalyzed Oxidative Coupling of Carboxylic Acids with N,N-Dialkylformamides: An Approach to the Synthesis of Amides

      Vol. 2013, Issue 14, 2941, Article first published online: 15 APR 2013

    4. Domino Reactions

      Diversely Substituted Triazolo[1,5-a][1,4]benzodiazepinones: A Post-Ugi Copper-Catalyzed Tandem Azide–Alkyne Cycloaddition/Ullmann C–N Coupling Approach (pages 1223–1227)

      Dipak D. Vachhani, Amit Kumar, Sachin G. Modha, Sunil K. Sharma, Virinder S. Parmar and Erik V. Van der Eycken

      Article first published online: 29 JAN 2013 | DOI: 10.1002/ejoc.201201587

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      The synthesis of triazolo[1,5-a][1,4]benzodiazepinones by employing a post-Ugi Cu-catalyzed tandem azide–alkyne cycloaddition (AAC)/Ullmann coupling strategy is elaborated. The intramolecular trapping of the N–Cu intermediate, formed by the CuAAC, leads to the formation of the C–N bond through Ullmann coupling and gives a novel and efficient route for the synthesis of triazolobenzodiazepinones.

    5. Low-Pressure [11C]Carbonylation

      Palladium-Mediated [11C]Carbonylation at Atmospheric Pressure: A General Method Using Xantphos as Supporting Ligand (pages 1228–1231)

      Kenneth Dahl, Magnus Schou, Nahid Amini and Christer Halldin

      Article first published online: 28 JAN 2013 | DOI: 10.1002/ejoc.201201708

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      The palladium-catalyzed [11C]carbonylation of aryl halides and triflates was achieved at atmospheric pressure by employing xantphos as the supporting ligand. Aryl halides were converted into their corresponding [11C]amides in good to excellent yields. The conditions were also successfully employed in the radiolabeling of an [11C]ester, a [11C]carboxylic acid, an [11C]aldehyde, and a [11C]ketone.

  6. Full Papers

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

      Effective and Versatile Strategy for the Total Solid-Phase Synthesis of Alkanethiols for Biological Applications (pages 1233–1239)

      Elisabet Prats-Alfonso, Sabine Oberhansl, Anna Lagunas, Elena Martínez, Josep Samitier and Fernando Albericio

      Article first published online: 25 JAN 2013 | DOI: 10.1002/ejoc.201201485

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      This paper describes a straightforward and inexpensive method based exclusively on solid-phase synthesis for the preparation of a variety of customized alkanethiols (ATs). The technique allows a variety of ATs to be obtained in only three steps, overcoming the difficulties encountered during their preparation in solution.

    2. Chiral Resorcin[4]arenes

      Inherently Chiral Resorcin[4]arenes with Urea and Amide Side Arms: Synthesis, Structure and Chiral Recognition (pages 1240–1245)

      Sebastian Wiegmann, Gaku Fukuhara, Beate Neumann, Hans-Georg Stammler, Yoshihisa Inoue and Jochen Mattay

      Article first published online: 18 JAN 2013 | DOI: 10.1002/ejoc.201201272

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      An inherently chiral aminomethylated resorcin[4]arene was used as a chiral scaffold to synthesize urea- and amide-functionalized derivatives. Introduction of chiral (S)-(–)-1-phenylethylurea side chains afforded diastereomeric macrocycle hosts; these were subjected to chiral recognition studies that revealed an R/S selectivity of 1.4 for an enantiomeric mandelic acid guest.

    3. Fused-Ring Systems

      Studies on the Regioselectivity of the Cyclization of Tryptophanol-Derived Oxazolopiperidone Lactams (pages 1246–1252)

      Mercedes Amat, Núria Llor, Fabiana Subrizi, Maria Pérez, Elies Molins and Joan Bosch

      Article first published online: 29 JAN 2013 | DOI: 10.1002/ejoc.201201508

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      Cyclizations on the lactam carbonyl from tryptophanol-derived oxazolopiperidone lactams have been studied. A pyridine ring fused to the piperidone moiety exerts a dramatic effect on the regioselectivity of the cyclization, leading exclusively to α-amidoalkylation products.

    4. N-Heterocyclic Carbene Ligands

      NHC PdII Complex Bearing 1,6-Hexylene Linker: Synthesis and Catalytic Activity in the Suzuki–Miyaura and Heck–Mizoroki Reactions (pages 1253–1261)

      Qing-Xiang Liu, Wei Zhang, Xiao-Jun Zhao, Zhi-Xiang Zhao, Meng-Chao Shi and Xiu-Guang Wang

      Article first published online: 21 JAN 2013 | DOI: 10.1002/ejoc.201200954

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      A new 1,6-hexylene-bridged bis-N-heterocyclic carbene PdII complex was prepared and characterized. The catalytic activities of this complex in Suzuki–Miyaura and Heck–Mizoroki reactions were investigated.

    5. Multicomponent Reactions

      Three-Component (Domino) Reaction Affording Substituted Pyrroloquinazolines: Cyclization Regioselectivity and Stereoselectivity (pages 1262–1270)

      Oldřich Paleta, Bohumil Dolenský, Jiří Paleček and Jaroslav Kvíčala

      Article first published online: 25 JAN 2013 | DOI: 10.1002/ejoc.201201356

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      The cyclization of 2-(aminomethyl)aniline, methyl 3,3,3-trifluoropyruvate, and various oxo compounds afforded linearly annulated pyrroloquinazolines as the major product along with angularly annulated products. The temperature was observed to affect the ratio of the two cyclization products. Some of the linear pyrroloquinazolines were stereoselectively didehydrogenated by the trifluoropyruvate.

    6. Modified Nucleosides

      Synthesis of Nucleobase-Functionalized Morpholino-Modified Nucleoside Monomers Through Palladium-Catalyzed Cross-Coupling Reactions (pages 1271–1286)

      Bappaditya Nandi, Sankha Pattanayak, Sibasish Paul and Surajit Sinha

      Article first published online: 18 JAN 2013 | DOI: 10.1002/ejoc.201201384

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      The synthesis of C-5-substituted cytidine and of C-8-substituted adenosine and guanosine morpholino nucleoside monomers by means of Pd-catalyzed cross-coupling (Sonogashira, Suzuki, and Heck) reactions is described. Various types of alkyne, aryl, and alkene group have been used to obtain diversely functionalized monomers from the corresponding iodo or bromo derivatives.

    7. Propargylation of Sulfinylimines

      Indium-Promoted Diastereo- and Regioselective Propargylation of Chiral Sulfinylimines (pages 1287–1295)

      M. Jesús García-Muñoz, Flavia Zacconi, Francisco Foubelo and Miguel Yus

      Article first published online: 24 JAN 2013 | DOI: 10.1002/ejoc.201201410

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      Indium-mediated propargylation of chiral N-tert-butanesulfinylimines with 3-bromo-1-trimethylsilyl-1-propyne in THF under sonication proceeds diastereoselectively in good yields.

    8. Iminosugar Synthesis

      Organocatalytic syn-Aldol Reactions of Hydroxy Ketones with (S)-Isoserinal: Asymmetric Synthesis of 6-Deoxy-1,5-iminohexitols and Related Compounds (pages 1296–1305)

      Cyril Nicolas, Roman Pluta, Monika Pasternak-Suder, Olivier R. Martin and Jacek Mlynarski

      Article first published online: 16 JAN 2013 | DOI: 10.1002/ejoc.201201413

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      A novel protocol for the preparation of 1,5,6-trideoxy-1,5-imino-L-mannitol and 1,5,6-trideoxy-1,5-imino-D-glucitol is reported. The key steps include organocatalyzed syn-selective direct aldol reaction of hydroxyacetone and CBz-protected isoserinal hydrate, followed by reductive amination/cyclization.

    9. Drug Discovery

      Complementary and Stereodivergent Approaches to the Synthesis of 5-Hydroxy- and 4,5-Dihydroxypipecolic Acids from Enantiopure Hydroxylated Lactams (pages 1306–1317)

      Dina Scarpi, Laura Bartali, Andrea Casini and Ernesto G. Occhiato

      Article first published online: 21 JAN 2013 | DOI: 10.1002/ejoc.201201429

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      The stereoselective synthesis of 5-hydroxy- and 4,5-dihydroxypipecolic acids was accomplished by sequential Pd-catalysed methoxycarbonylation and stereoselective reduction of enantiopure hydroxylated lactam-derived enol phosphates obtained from both enantiomers of commercially available γ-hydroxymethyl-γ-butyrolactone and 2-deoxyribose.

    10. 9,10-Anthraquinones

      Synthesis of Macrosporin and Related 9,10-Anthraquinones by Biomimetic Polyketide Aromatization and Cyclization of 6-Benzylresorcylates (pages 1318–1326)

      Jens Cordes and Anthony G. M. Barrett

      Article first published online: 24 JAN 2013 | DOI: 10.1002/ejoc.201201480

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      A new synthetic approach to 9,10-anthraquinones was developed. Selective Claisen condensation of an allyl γ-dioxinyl-β-oxo ester with arylacetyl chlorides, Pd-catalyzed deallylation, decarboxylation and aromatization gave 6-(arylmethyl)resorcylates. Subsequent acid-mediated cyclization and oxidation with CAN gave target anthraquinones, one of these being the fungal natural product macrosporin.

    11. “On-Water” Chemistry

      Michael Additions in Aqueous Media: “On-Water” and “In-Water” Processes from α-Nitro Ketones and Their Anions (pages 1327–1336)

      Giorgio Giorgi, Pilar López-Alvarado, Sonia Miranda, Jean Rodriguez and J. Carlos Menéndez

      Article first published online: 24 JAN 2013 | DOI: 10.1002/ejoc.201201431

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      α-Nitrocycloalkanones gave high-yielding “on-water” Michael addition reactions to α,β-unsaturated aldehydes and ketones. The scope of the method was extended to cyclic enones and unsaturated esters, nitriles and sulfones by use of very dilute aqueous solutions of potassium carbonate as the reaction media.

    12. Heterogeneous Cross-Coupling

      A Phosphane-Free, Atom-Efficient Cross-Coupling Reaction of Triarylbismuths with Acyl Chlorides Catalyzed by MCM-41-Immobilized Palladium Complex (pages 1337–1345)

      Hong Zhao, Lin Yin and Mingzhong Cai

      Article first published online: 25 JAN 2013 | DOI: 10.1002/ejoc.201201432

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      The first phosphane-free, heterogeneous, atom-efficient cross-coupling reaction of triarylbismuth compounds and acyl chlorides was achieved in N-methylpyrrolidone with Bu3N as the base at 80 °C in the presence of 1.5 mol-% MCM-41-immobilized bidentate nitrogen palladium complex [MCM-41–2N-Pd(OAc)2] to yield a variety of unsymmetrical biaryl ketones in good to excellent yields.

    13. Natural Product Synthesis

      Concise Total Syntheses of Dipiperidine Alkaloids Virgidivarine and Virgiboidine through Ru-Mediated Ene-Ene-Yne Ring Rearrangement Metathesis (RRM) (pages 1346–1355)

      Steffen Kress, Jochen Weckesser, Sabrina Renate Schulz and Siegfried Blechert

      Article first published online: 17 JAN 2013 | DOI: 10.1002/ejoc.201201516

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      Five@Once: A new method to access dipiperidine and piperidino-quinolizidine alkaloids was established within the total syntheses of virgidivarine (1) and virgiboidine (2). The key step includes a Ru-mediated intramolecular (tandem) ene-ene-yne ring-rearrangement metathesis/oxidation process, in which a sequence of five reactions occur in a single vessel with one catalyst source.

    14. Total Synthesis

      Studies on the Total Synthesis of Hirtellanine A: Regioselective Synthesis of Benzopyran (pages 1356–1366)

      Shu-yan Zheng, Xiao-ping Li, Hong-sheng Tan, Chun-hui Yu, Jing-hua Zhang and Zheng-wu Shen

      Article first published online: 24 JAN 2013 | DOI: 10.1002/ejoc.201201339

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      The total synthesis of Hirtellanine A was achieved. The synthesis featured a one-pot, tandem acid-mediated deprotection and tautomerization cascade for the construction of the coumaronochromone motif, and a regioselective Claisen rearrangement for the benzopyran construction.

    15. C–H Activation

      Palladium-Catalyzed ortho-Aroylation of 2-Arylbenzothiazoles and 2-Arylbenzoxazoles with Aldehydes (pages 1367–1376)

      Arghya Banerjee, Sourav Kumar Santra, Srimanta Guin, Saroj Kumar Rout and Bhisma K. Patel

      Article first published online: 16 JAN 2013 | DOI: 10.1002/ejoc.201201503

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      An efficient protocol for the ortho-aroylation of 2-arylbenzothiazoles and 2-arylbenzoxazoles has been developed using aldehydes as the aroyl source. This Pd-catalyzed C–H bond functionalization occurs in the presence of tert-butyl hydroperoxide, and a variety of functional groups on the 2-arylbenzothiazoles, 2-arylbenzoxazoles, and aldehydes are tolerated under the reaction conditions.

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