European Journal of Organic Chemistry

Cover image for Vol. 2016 Issue 21

July 2016

Volume 2016, Issue 21

Pages 3457–3656

  1. Front Cover

    1. Top of page
    2. Front Cover
    3. News
    4. Microreviews
    5. Communications
    6. Full Papers
    1. You have free access to this content
      Front Cover: Cyclisation of Disulfide-Rich Conotoxins in Drug Design Applications (Eur. J. Org. Chem. 21/2016) (page 3457)

      Xiaosa Wu, Yen-Hua Huang, Quentin Kaas and David J. Craik

      Version of Record online: 21 JUL 2016 | DOI: 10.1002/ejoc.201670211

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      The cover picture shows a drawing of the marine cone snail Conus victoriae and the structure of a conotoxin found in its venom used for prey capture. Conotoxins have great potential as drugs for the treatment of pain. The image is based on an original watercolor painting by Peta Harvey and a structural image by Yen-Hua Huang from the laboratory of David Craik. The Microreview by D. J. Craik et al. on p. 3462 ff.

  2. News

    1. Top of page
    2. Front Cover
    3. News
    4. Microreviews
    5. Communications
    6. Full Papers
  3. Microreviews

    1. Top of page
    2. Front Cover
    3. News
    4. Microreviews
    5. Communications
    6. Full Papers
    1. Cyclisation of Conotoxin

      Cyclisation of Disulfide-Rich Conotoxins in Drug Design Applications (pages 3462–3472)

      Xiaosa Wu, Yen-Hua Huang, Quentin Kaas and David J. Craik

      Version of Record online: 1 JUL 2016 | DOI: 10.1002/ejoc.201600402

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      Conotoxins specifically target a wide range of ion channel subtypes but can be susceptible to degradation in biological fluids, which is a challenge in their use as drug leads. Backbone cyclisation can overcome this challenge and improve the biopharmaceutical properties of conotoxins.

  4. Communications

    1. Top of page
    2. Front Cover
    3. News
    4. Microreviews
    5. Communications
    6. Full Papers
    1. Dienes from Diacids

      Enzymatic Oxidative Tandem Decarboxylation of Dioic Acids to Terminal Dienes (pages 3473–3477)

      Alexander Dennig, Sara Kurakin, Miriam Kuhn, Andela Dordic, Mélanie Hall and Kurt Faber

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600358

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      An enzymatic sequential two-step oxidative decarboxylation of C7–C18 dicarboxylic acids by using the monooxygenase OleT gives terminal C5–C16 dienes; NAD = nicotinamide adenine dinucleotide.

    2. One-Pot Reactions

      Synthesis of Asymmetrical-Terminally Bifunctionlized Alkanes by Sequential Suzuki–Miyaura Coupling Using B-Thexylboracyclanes (pages 3478–3481)

      Ryota Suzuki, Shinichiro Fuse and Hiroshi Tanaka

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600392

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      A one-pot, sequential Suzuki–Miyaura coupling using B-thexylboracyclanes is reported, which selectively provided acyclic boric acids. They subsequently underwent a second Suzuki–Miyaura coupling under harsher conditions to afford asymmetrical-terminally bifunctionlized alkanes in a one-pot reaction.

    3. Modified Nucleosides

      S-Geranylated 2-Thiouridines of Bacterial tRNAs: Chemical Synthesis and Physicochemical Properties (pages 3482–3485)

      Grazyna Leszczynska, Klaudia Sadowska, Paulina Bartos, Barbara Nawrot and Elzbieta Sochacka

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600519

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      5-Substituted S-geranyl-2-thiouridines are modified nucleosides present in the first (wobble) position of bacterial tRNA anticodons. Geranylated nucleosides are obtained by S-alkylation of suitably protected 2-thiouridines. The influence of the S-geranyl moiety on the hydrophobic and conformational properties of modified nucleosides is determined and compared to that of parent 2-thiouridines.

    4. Heterocycles

      Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinoline and Ethyl (Z)-3-Acetoxy-3-tosylpent-4-enoate through Tertiary-Amine-Catalyzed [3+2] Annulation (pages 3486–3490)

      Yu Lei, Jiao-Jiao Xing, Qin Xu and Min Shi

      Version of Record online: 4 JUL 2016 | DOI: 10.1002/ejoc.201600577

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      1,4-Diazabicyclo[2.2.2]octane (DABCO) catalyzed divergent [3+2] annulations of C,N-cyclic azomethine imines with δ-acetoxyallenoates afford 5,6-dihydropyrazolo[5,1-a]isoquinolines and ethyl (Z)-3-acetoxy-3-tosylpent-4-enoates concurrently in a one-pot manner under mild conditions. The cycloaddition reaction provides a highly efficient method to construct dinitrogen-fused heterocycles.

    5. Fluorination

      A Mild Method for the Direct Fluorination of Pyrroles by Using a Lipophilic Anionic Phase-Transfer Catalyst (pages 3491–3494)

      Kenichi Hiramatsu and Hirokazu Tamamura

      Version of Record online: 4 JUL 2016 | DOI: 10.1002/ejoc.201600570

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      A mild fluorination method for pyrroles has been developed, which is based on anionic phase-transfer catalysis by using Selectfluor, a lipophilic phosphoric acid, and a base in an apolar solvent. The thus obtained fluorinated pyrroles, bearing functional groups, are sought-after building blocks in medicinal chemistry.

    6. Plant Hormone Synthesis

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      Strigolactone Analogues with a D-Ring Modified at C-2 (pages 3495–3499)

      Alinanuswe S. Mwakaboko and Binne Zwanenburg

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600576

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      Strigolactones with a D-ring modified at C-2 were prepared and bioassayed for germination of seeds of parasitic weeds. The methyl at C-2 does not influence the activity, which is relevant for the mode of action of strigolactones.

    7. Allylation

      Palladium-Catalyzed Diastereoselective α-Allylation of Chiral Sulfinimines (pages 3500–3504)

      Jiangnan Li, Shende Jiang, George Procopiou, Robert A. Stockman and Guang Yang

      Version of Record online: 4 JUL 2016 | DOI: 10.1002/ejoc.201600615

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      The first highly diastereoselective palladium(0)-catalyzed α-allylation of simple ketones by using tert-butanesulfinamide as a chiral auxiliary is reported. The products are obtained in high chemical yields with good diastereoselectivities and excellent regiocontrol. The chiral auxiliary can be removed in almost quantitative yield without racemization.

    8. Peptide Synthesis

      Peptide Mechanosynthesis by Direct Coupling of N-Protected α-Amino Acids with Amino Esters (pages 3505–3508)

      Vincent Porte, Marion Thioloy, Titouan Pigoux, Thomas-Xavier Métro, Jean Martinez and Frédéric Lamaty

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600617

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      Liquid-assisted grinding (LAG) enables intensive, scalable, and environmentally benign production of peptides by direct coupling of N-protected α-amino acids with amino esters mediated by N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide. Association of ball-milling, judiciously selected liquid additive, and reagents with reduced safety profiles furnish the peptides in good to excellent yields.

    9. Cross-Coupling

      Palladium-Catalyzed Regioselective Dehydrogenative C–H/C–H Cross-Coupling of Pyrroles and Pyridine N-Oxides (pages 3509–3513)

      Shanshan Liu and C. Christoph Tzschucke

      Version of Record online: 4 JUL 2016 | DOI: 10.1002/ejoc.201600680

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      More than an oxidant: In the palladium-catalyzed C–H/C–H cross-coupling of pyrroles and pyridine N-oxides, the regioselectivity depends on the oxidation co-catalyst. β-Selective arylation of protected pyrroles is achieved by use of substoichiometric Cu(OAc)2·H2O and air as the oxidant, whereas α-selectivity is obtained by using AgOAc as the oxidant.

    10. Biobased Organocatalysts

      Imidazolium and Potassium Hydrogen Carbonate Salts as Ecofriendly Organocatalysts for Oxazolidinone Synthesis (pages 3514–3518)

      Antoine H. Fournier, Guillaume de Robillard, Charles H. Devillers, Laurent Plasseraud and Jacques Andrieu

      Version of Record online: 4 JUL 2016 | DOI: 10.1002/ejoc.201600550

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      The imidazolium hydrogen carbonate salt is a more efficient catalyst than its potassium analogue to convert amino alcohols and diethyl carbonate (DEC) into cyclic oxazolidinones, which are chemical intermediates in the production of antibiotics. This biobased catalyst can be recovered and reused without sacrificing its catalytic performance.

  5. Full Papers

    1. Top of page
    2. Front Cover
    3. News
    4. Microreviews
    5. Communications
    6. Full Papers
    1. Retro-Diels–Alder Reactions

      A Domino Ring-Closure Followed by Retro-Diels–Alder Reaction for the Preparation of Pyrimido[2,1-a]isoindole Enantiomers (pages 3519–3527)

      Beáta Fekete, Márta Palkó, István Mándity, Matti Haukka and Ferenc Fülöp

      Version of Record online: 24 JUN 2016 | DOI: 10.1002/ejoc.201600434

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      Racemic and enantiomeric pentacyclic isoindoloquinazoline derivatives were prepared by a domino ring-closure reaction starting from β-amino hydroxamic acids. A microwave-induced retro-Diels–Alder reaction of these derivatives yielded racemic and enantiopure dihydropyrimido[2,1-a]isoindoles

    2. Alkyne Hydration

      Unexpected Hydration of a Triple Bond During DNA Synthesis: Conjugating 3-(Pyren-1-ylethynyl)indole to DNA for Triplex Studies (pages 3528–3535)

      Maha I. Fatthalla and Erik B. Pedersen

      Version of Record online: 19 JUN 2016 | DOI: 10.1002/ejoc.201600287

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      This work demonstrates a risk for unwanted hydration of a triple bond into the corresponding ketone during DNA synthesis. This is exemplified by the synthesis of 3-(pyren-1-ylethynyl)indole as an intercalator linked to a DNA backbone.

    3. Sensitizers

      Effect of Thiophene Spacer Position in Carbazole-Based Dye-Sensitized Solar Cells on Photophysical, Electrochemical and Photovoltaic Properties (pages 3536–3549)

      Ruslan Samae, Panida Surawatanawong, Utt Eiamprasert, Songyos Pramjit, Laksana Saengdee, Pramuan Tangboriboonrat and Supavadee Kiatisevi

      Version of Record online: 23 JUN 2016 | DOI: 10.1002/ejoc.201600353

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      Five new carbazole-based dyes were synthesized. Whereas redshifted spectra can be achieved by inserting a thiophene next to the acceptor, the inclusion of a thiophene as part of the donor causes hyperchromicity but almost no shift in λmax. The power conversion efficiency of the DSSCs depends on the position of the thiophene.

    4. Palladium Cross-Coupling

      Regioselective Synthesis of 2,4-Substituted Pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyrimidines through Sequential Pd-Catalyzed Arylation and SNAr Reactions (pages 3550–3558)

      Rabia Belaroussi, Ahmed El Hakmaoui, Mohamed Akssira, Gérald Guillaumet and Sylvain Routier

      Version of Record online: 4 JUL 2016 | DOI: 10.1002/ejoc.201600356

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      The synthesis and regioselective functionalization of rare 2,4-disubstituted-pyrido[1′,2′:1,5]pyrazole[3,4-d]pyrimidine derivatives is reported. C-4 amination or (het)arylations are performed by halogen displacement or by “one-pot” amide C–O activation. Finally, desulfurative Liebeskind–Srogl reactions under microwave irradiation afford the envisioned C-2 and C-4 functionalized library.

    5. C–C Coupling

      A Metal-Free Oxidative Cross-Dehydrogenative Coupling of N-Aryl Tetrahydroisoquinolines and 2-Methylazaarenes Using a Recyclable Oxoammonium Salt as Oxidant in Aqueous Media (pages 3559–3567)

      Li Fang, Zhenhua Li, Zhijiang Jiang, Zhiyong Tan and Yuanyuan Xie

      Version of Record online: 4 JUL 2016 | DOI: 10.1002/ejoc.201600423

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      A metal-free oxidative cross-dehydrogenative coupling of N-aryl tetrahydroisoquinolines and 2-methylazaarenes using recyclable oxidant 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate in water under mild conditions has been developed.

    6. Gabosines

      Filling Some Blanks in a Divergent Approach to Gabosines: Enantioselective Synthesis of (–)-Epiepoxydon, (+)-Phyllostine, (–)-Gabosine D, and (–)-Gabosine E (pages 3568–3574)

      Miguel Ángel Fresneda, Ramon Alibés, Pau Bayón and Marta Figueredo

      Version of Record online: 4 JUL 2016 | DOI: 10.1002/ejoc.201600492

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      The levorotatory enantiomers of gabosines D and E were synthesized through a divergent approach that could equally well be applied to the synthesis of the dextrorotatory enantiomers. A branching in the sequence also allowed the synthesis of the anhydrogabosines (–)-epiepoxydon and (+)-phyllostine.

    7. γ-Keto Sulfones

      Direct Synthesis of γ-Keto Sulfones from Allylic Alcohols: One-Pot Palladium(II)-Catalyzed Generation of Enones Followed by Water-Mediated 1,4-Addition of Organosulfinates (pages 3575–3583)

      Mari Vellakkaran, Murugaiah M. S. Andappan, Kommu Nagaiah and Jagadeesh Babu Nanubolu

      Version of Record online: 4 JUL 2016 | DOI: 10.1002/ejoc.201600494

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      Allylic alcohols are exploited as synthetic precursors of γ-keto sulfones. The reaction involves the one-pot generation of α,β-enones in situ from the allylic alcohols by using a PdII–dioxygen catalytic system and subsequent sulfa-Michael addition in the presence of water.

    8. Acylation

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      Efficient O-Acylation of Alcohols and Phenol Using Cp2TiCl as a Reaction Promoter (pages 3584–3591)

      María Jesús Durán-Peña, José Manuel Botubol-Ares, James R. Hanson, Rosario Hernández-Galán and Isidro G. Collado

      Version of Record online: 4 JUL 2016 | DOI: 10.1002/ejoc.201600496

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      A set of primary, secondary, and tertiary alcohols, and phenol, have been converted into the corresponding esters using a substoichiometric amount of bis(cyclopentadienyl)titanium(III) chloride in good yields and under mild reaction conditions.

    9. Tandem C- and O-Amidoalkylation

      Bi(OTf)3-Catalysed Access to 2,3-Substituted Isoindolinones and Tricyclic N,O-Acetals by Trapping of Bis-N-Acyliminium Species in a Tandem Process (pages 3592–3602)

      Ahmed Aliyenne, Frédéric Pin, Vijaykumar D. Nimbarte, Ata Martin Lawson, Sébastien Comesse, Morgane Sanselme, Vincent Tognetti, Laurent Joubert and Adam Daïch

      Version of Record online: 24 JUN 2016 | DOI: 10.1002/ejoc.201600530

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      Isoindolinones and tricyclic N,O-acetals are obtained from bis-N-acyliminium precursors and assorted nucleophiles using catalytic Bi(OTf)3. The reactions proceed, respectively, through a double amidoalkylation or tandem π-cyclisation/α-oxa-amidoalkylation. Mechanistic aspects of the tandem chemistry are supported by DFT calculations and its utility in RCM and Click reactions illustrated.

    10. Tetracyclic Compounds

      Regio- and Stereoselective Synthesis of Valuable Tetracyclic Compounds by Intramolecular Diels–Alder Reactions between Furan and Cyclopropene Moieties (pages 3603–3610)

      Junhao Hu, Zhenghai Wang and Yuefa Gong

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600535

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      A direct regio- and diastereoselective synthetic route for valuable tetracyclic compounds that employs intramolecular Diels–Alder reactions between furanyl and electron-deficient cyclopropene groups has been developed. The reaction readily proceeds under mild basic conditions to afford potentially bioactive ring-fused compounds in moderate to high yields with high diastereoselectivities.

    11. C–H Activation

      Rhodium-Catalyzed Vinylic C–H Functionalization of Enol Carbamates with Maleimides (pages 3611–3618)

      Satyasheel Sharma, Sang Hoon Han, Hyeim Jo, Sangil Han, Neeraj Kumar Mishra, Miji Choi, Taejoo Jeong, Jihye Park and In Su Kim

      Version of Record online: 24 JUN 2016 | DOI: 10.1002/ejoc.201600558

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      The rhodium(III)-catalyzed direct C–H alkylation of enol carbamates with a range of maleimides is described. With the assistance of the carbamoyl directing group, this reaction provides biologically relevant succinimide compounds by proceeding through a C–Rh addition and subsequent protonation pathway.

    12. Organocatalysis

      Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans (pages 3619–3624)

      Kevin Kasten, David B. Cordes, Alexandra M. Z. Slawin and Andrew D. Smith

      Version of Record online: 23 JUN 2016 | DOI: 10.1002/ejoc.201600583

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      The quinidine-catalysed enantioselective formal [4+2]-cycloaddition of ethyl 2,3-butadienoate with a range of 1,1,1-trifluoro- and 4,4,4-trifluorobutenones is demonstrated for the preparation of stereodefined C(6) – and 4-trifluoromethyl-substituted dihydropyrans (up to 98 % ee and 81 % yield).

    13. Pd-Catalyzed Directed Chlorination

      Pd-Catalyzed Directed Chlorination of Unactivated C(sp3)–H Bonds at Room Temperature (pages 3625–3630)

      Heng-Ying Xiong, Dominique Cahard, Xavier Pannecoucke and Tatiana Besset

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600600

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      A Pd-catalyzed directed chlorination of unactivated C(sp3)–H bonds has been developed. By using a bidentate directing group, the chlorination of aliphatic amides was achieved in moderate to good yields in the presence of N-chlorosuccinimide (NCS) at room temperature. This approach offers a new access to valuable chlorinated molecules, key building blocks for bulk and fine chemical industry.

    14. Ring-Strain Effect

      Ring-Strain Effects in Base-Induced Sommelet–Hauser Rearrangement: Application to Successive Stereocontrolled Transformations (pages 3631–3641)

      Eiji Tayama, Kazutoshi Watanabe and Yoshihiro Matano

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600611

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      The base-induced Sommelet–Hauser rearrangement of azetidine-2-carboxylic acid ester-derived ammonium salts was successfully demonstrated. The ring-strain of four-membered N-heterocycles enables efficient generation of the desired ylide intermediate and enhanced rates for the Sommelet–Hauser rearrangement.

    15. Unprotected Sugar Utilization

      Diversity-Oriented Synthesis and Biological Evaluation of Iminosugars from Unprotected 2-Deoxy-d-ribose (pages 3642–3649)

      Maciej Malinowski, Tomasz Rowicki, Patrycja Guzik, Monika Wielechowska, Anna Sobiepanek and Wojciech Sas

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600459

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      The diversity-oriented synthesis of iminosugars with various heterocyclic cores has been achieved starting from 2-deoxy-dribose with no need for sugar protection in any step. Selective cleavage of the triol to the α-hydroxy aldehyde with no racemization of the α-stereocenter was accomplished with 1 equiv. of sodium periodate at low temperature.

    16. Oxazolidinones Synthesis

      Selective Synthesis of 5-Substituted N-Aryloxazolidinones by Cycloaddition Reaction of Epoxides with Arylcarbamates Catalyzed by the Ionic Liquid BmimOAc (pages 3650–3656)

      Elnazeer H. M. Elageed, Bihua Chen, Binshen Wang, Yongya Zhang, Shi Wu, Xiuli Liu and Guohua Gao

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600474

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      5-Substituted N-aryloxazolidinones have been selectively synthesized by the coupling of epoxides with arylcarbamates catalyzed by ionic liquids. Under the optimal conditions, BmimOAc catalyzed the formation of 5-substituted N-aryloxazolidinones in excellent yields. 1H NMR spectroscopy and DFT calculations indicate the cooperative activation of the substrates by BmimOAc through hydrogen bonding.

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