European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 7

March 2015

Volume 2015, Issue 7

Pages 1371–1612

  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
      Structure–Activity Relationships in the Domain of Odorants Having Marine Notes (Eur. J. Org. Chem. 7/2015)

      Jean-Marc Gaudin and Jean-Yves de Saint Laumer

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201590015

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      The cover picture shows the model used by the authors to find a new class of molecules that have marine, watery olfactory notes, surfing on the big wave of success of this trend for both men's and women's perfumes. Continuing their efforts in this domain, the authors demonstrate that the seven-membered ring with the ketone functional group of the Calone 1951® family can be replaced by a five-membered ring carrying an aldehyde function. Details are discussed in the article by J.-M. Gaudin and J.-Y. de Saint Laumer on 1437 ff. The authors would like to warmly thank H. Fabreguettes for his assistance for this cover picture.

  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. 7/2015 (pages 1371–1379)

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201590017

  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. Frondosin Natural Products

      The Frondosins: An Unusual Synthetic and Stereochemical Journey (pages 1387–1401)

      Michael D. VanHeyst and Dennis L. Wright

      Article first published online: 28 NOV 2014 | DOI: 10.1002/ejoc.201403116

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      The first two syntheses of (+)-frondosin B, by Danishefsky and by Trauner, gave conflicting assignments for the single stereocenter at C8. Ensuing syntheses of frondosins B and A resolved this conflict and established that (+)-frondosin B is the R enantiomer. Wright's group showed that a late-stage stereochemical inversion occurred in a common intermediate of both their and Trauner's syntheses.

  5. Short Communications

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

      Photochromism of Acetyl-Cyclophanochromene: Intriguing Stabilization of Photogenerated Colored o-Quinonoid Intermediates (pages 1403–1408)

      Susovan Mandal, Arindam Mukhopadhyay and Jarugu Narasimha Moorthy

      Article first published online: 27 JAN 2015 | DOI: 10.1002/ejoc.201403403

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      A combination of the phane effect, that is, through-space π-electron delocalization, and electrophile···nucleophile interactions results in remarkable persistence of the photogenerated colored o-quinonoid intermediate of acetyl-cyclophanochromene.

    2. Helicene Synthesis

      Enantioselective Synthesis, Crystal Structure, and Photophysical Properties of a 1,1′-Bitriphenylene-Based Sila[7]helicene (pages 1409–1414)

      Koichi Murayama, Yasuaki Oike, Seiichi Furumi, Masayuki Takeuchi, Keiichi Noguchi and Ken Tanaka

      Article first published online: 22 JAN 2015 | DOI: 10.1002/ejoc.201403565

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      A 1,1′-bitriphenylene-based sila[7]helicene was synthesized with a high ee value by enantioselective double [2+2+2] cycloaddition of a biaryl-linked tetrayne and a silicon-linked bis(propargylic alcohol) as a key step. This sila[7]helicene exhibited a relatively high fluorescence quantum yield and circularly polarized luminescence activity.

    3. Multicomponent Reactions

      FeCl3-Catalyzed SF5-Containing Quinoline Synthesis: Three-Component Coupling Reactions of SF5-Anilines, Aldehydes and Alkynes (pages 1415–1418)

      Xueling Mi, Jing Chen and Lijin Xu

      Article first published online: 29 JAN 2015 | DOI: 10.1002/ejoc.201403613

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      The iron-catalyzed three-component coupling/hydroarylation/dehydrogenation reaction of SF5-anilines, aldehydes and alkynes provides an efficient route to SF5-containing quinolines.

    4. Synthesis of Isoxazolines

      Oxime-Mediated Oxychlorination and Oxybromination of Unactivated Olefins (pages 1419–1422)

      Kui-Yong Dong, Hai-Tao Qin, Feng Liu and Chen Zhu

      Article first published online: 23 JAN 2015 | DOI: 10.1002/ejoc.201403538

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      One to two: An oxime-mediated oxychlorination and oxybromination of unactivated olefins relying on palladium catalysis has been developed. A wide range of chlorinated and brominated isoxazolines has been synthesized in moderate to good yields.

    5. Fullerenes

      Efficient Microwave-Assisted Synthesis of PCBM Methanofullerenes (C60 and C70) (pages 1423–1427)

      Caroline Hadad, Zois Syrgiannis, Aurelio Bonasera and Maurizio Prato

      Article first published online: 22 JAN 2015 | DOI: 10.1002/ejoc.201403563

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      PC61BM and PC71BM fullerene mono-adducts, and also a series of bis-adduct PCBM-like derivative mixtures, were successfully prepared by a one-step cyclopropanation reaction under microwave irradiation. All products were obtained in good yields, in short time, during which isomerization of the open [5,6] to the closed [6,6] form takes place in situ.

    6. Oxidative Amidation

      Iodine-Promoted Oxidative Amidation of Terminal Alkenes – Synthesis of α-Ketoamides, Benzothiazoles, and Quinazolines (pages 1428–1432)

      Ramesh Deshidi, Shekaraiah Devari and Bhahwal Ali Shah

      Article first published online: 27 JAN 2015 | DOI: 10.1002/ejoc.201403547

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      A novel metal-free strategy for oxidative amidation of terminal alkenes using I2/DMSO for the synthesis of α-ketoamides has been developed. Intriguingly, the use of tert-butylhydroperoxide (TBHP) as co-oxidant can facilitate the synthesis of α-ketoamides at room temperature without any solvent, whereas for reaction with primary amines SeO2 is required as oxidizing agent.

    7. Protecting Groups

      Fmox: A Base-Labile Aldehyde Protecting Group (pages 1433–1436)

      Frederik Diness and Morten Meldal

      Article first published online: 27 JAN 2015 | DOI: 10.1002/ejoc.201403643

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      The Fmox group [3-Fmoc-(1,3)-oxazinane] is a novel base-labile protecting group for the protection of aldehydes while manipulating other functional groups e.g., amines. It is completely removed under mild basic conditions under which a range of other aldehyde protecting groups are fully stable. Studies on the introduction and removal of Fmox and other aldehyde protecting groups have provided new mechanistic insight.

  6. Full Papers

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

      Structure–Activity Relationships in the Domain of Odorants Having Marine Notes (pages 1437–1447)

      Jean-Marc Gaudin and Jean-Yves de Saint Laumer

      Article first published online: 23 JAN 2015 | DOI: 10.1002/ejoc.201403365

      Thumbnail image of graphical abstract

      A new class of molecules having marine, watery olfactory notes has been discovered. A model built from the Calone 1951® family shows that the seven-membered ring with a ketone group can be replaced by a five-membered ring bearing an aldehyde. Interestingly, as a side benefit, a methyl carbonate compound has been synthesized that is olfactively very close to vanillin and has interesting properties.

    2. Thiodisaccharide Sulfoxides

      Thiodisaccharide Sulfoxides: Absolute Configuration of the SO Sulfur Atom and Influence on the Biological Activity towards the β-Galactosidase from E. coli (pages 1448–1455)

      Juan P. Colomer, María Ángeles Canales Mayordomo, Beatriz Fernández de Toro, Jesús Jiménez-Barbero and Oscar Varela

      Article first published online: 22 JAN 2015 | DOI: 10.1002/ejoc.201403609

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      The absolute configurations of the sulfur stereocenters of (1[RIGHTWARDS ARROW]4)-thiodisaccharide S-oxides have been assigned on the basis of the NMR chemical shifts of the β protons with respect to the S=O group (3-H and 5-H). Each diastereoisomer displays different biological activities, as inhibitors or substrates, of the β-galactosidase from E. coli.

    3. Synthesis of Substituted Dibenz[a,c]anthracenes and an Investigation of Their Liquid-Crystalline Properties (pages 1456–1463)

      Katie M. Psutka, Joshua Williams, Joseph A. Paquette, Oliver Calderon, Kevin J. A. Bozek, Vance E. Williams and Kenneth E. Maly

      Article first published online: 22 JAN 2015 | DOI: 10.1002/ejoc.201403504

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      The synthesis of a series of novel dibenz[a,c]anthracenes is described. The dicyano-substituted derivatives exhibit columnar mesophases and are consistent with antiparallel stacking and a tilted arrangement within the columns.

    4. Natural Product Synthesis

      First Total Synthesis of Piperenol B and Configuration Revision of the Enantiomers Piperenol B and Uvarirufol A (pages 1464–1471)

      Thomas C. Fischer, Bruno Cerra, Michael J. Fink, Florian Rudroff, Ernst Horkel and Marko D. Mihovilovic

      Article first published online: 27 JAN 2015 | DOI: 10.1002/ejoc.201403582

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      The first total synthesis of piperenol B, a polyoxygenated cyclohexene natural product from Piper cubeb, has been developed starting with the multi-ten-gram scale enzymatic dihydroxylation of sodium benzoate. The originally predicted absolute configurations of piperenol B and its enantiomer uvarirufol A were eventually revised based on this synthesis and NMR analysis of late-stage Mosher's esters.

    5. Conformational Probes

      Stereoselective Synthesis of Boat-Locked Glycosides Designed as Glycosyl Hydrolase Conformational Probes (pages 1472–1484)

      Emilie Thiery, Jérémy Reniers, Johan Wouters and Stéphane P. Vincent

      Article first published online: 26 JAN 2015 | DOI: 10.1002/ejoc.201403363

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      A general method for the preparation of galactose derivatives locked in a 1,4B boat conformation has been developed. The boat scaffold was stereoselectively functionalized at the C-1′ position by aliphatic and aromatic groups along with azido or hydroxy groups. These molecules have been designed to probe the conformational itinerary of the substrate of glycosyl-processing enzymes.

    6. Metathesis Chemistry

      Synthesis of Acyloxy-Semicyclic Dienes Using an Enyne Metathesis/Ring Closing Metathesis Approach (pages 1485–1490)

      Jui Thiang Brian Kueh, Lindon W. K. Moodie, Nigel T. Lucas and David S. Larsen

      Article first published online: 20 JAN 2015 | DOI: 10.1002/ejoc.201403482

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      An enyne metathesis/ring closing metathesis (EM/RCM) sequence was developed to allow convenient access to acyloxy-semicyclic dienes not available from the cross metathesis of vinyl esters with the termini of 1,3-dienes. The prepared acyloxy-semicyclic dienes constitute useful reactants in Diels–Alder cycloadditions.

    7. Flow Chemistry

      You have full text access to this OnlineOpen article
      Generation and Trapping of Ketenes in Flow (pages 1491–1499)

      Cyril Henry, David Bolien, Bogdan Ibanescu, Sally Bloodworth, David C. Harrowven, Xunli Zhang, Andy Craven, Helen F. Sneddon and Richard J. Whitby

      Article first published online: 20 JAN 2015 | DOI: 10.1002/ejoc.201403603

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      Ketenes are generated under flow conditions by thermal sigmatropic rearrangement of alkoxyalkynes. Subsequent trapping with amines or alcohols gives amide or ester products, respectively. Inline monitoring by IR spectroscopy and offline analysis by 1H NMR spectroscopy allow the rapid study of kinetics and optimisation of the reaction.

    8. β-Amino Esters

      Studies on N-Activation for the Lipase-Catalyzed Enantioselective Preparation of β-Amino Esters from 4-Phenylazetidin-2-one (pages 1500–1506)

      Riku Sundell and Liisa T. Kanerva

      Article first published online: 27 JAN 2015 | DOI: 10.1002/ejoc.201403467

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      The effect of N-substitution on the enantioselective lipase-catalyzed ring-opening of 4-phenylazetidin-2-one was examined by alcoholysis reactions in dry organic solvents. The nature of the N-substituent dramatically affected the reactivity of the β-lactam. Through this approach, N-acylated β-amino esters were formed in good yields and with excellent enantiopurity.

    9. Amination

      Copper-Catalyzed Direct Amination of 1,2,3-Triazole N-Oxides by C–H Activation and C–N Coupling (pages 1507–1515)

      Jiayi Zhu, Yubo Kong, Feng Lin, Baoshuang Wang, Zhengwang Chen and Liangxian Liu

      Article first published online: 23 JAN 2015 | DOI: 10.1002/ejoc.201403583

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      A facile, efficient, and practical method for the copper-catalyzed direct C–H amination of 2-aryl-1,2,3-triazole N-oxides with various amines, including primary and secondary aliphatic and aromatic amines, has been developed. Furthermore, the targeted N+–O bond cleavage is observed during the reaction and, thus, an additional deoxygenation step is obviated.

    10. Natural Products

      The Diels–Alder Approach to Δ9-Tetrahydrocannabinol Derivatives (pages 1516–1524)

      Franziska Gläser, Manuel C. Bröhmer, Thomas Hurrle, Martin Nieger and Stefan Bräse

      Article first published online: 29 JAN 2015 | DOI: 10.1002/ejoc.201403379

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      Molecules with structures similar to THC, such as nabilone, HU-210, or cannabidiol, show high pharmacological activities, and are used in chemotherapy or as appetite stimulants for AIDS patients. Therefore we have investigated various synthetic pathways using simple reaction methods to get access to a range of new THC derivatives.

    11. Organozinc Chemistry

      Variations in the Blaise Reaction: Conceptually New Synthesis of 3-Amino Enones and 1,3-Diketones (pages 1525–1532)

      H. Surya Prakash Rao and Nandurka Muthanna

      Article first published online: 22 JAN 2015 | DOI: 10.1002/ejoc.201403402

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      A variety of aryl/heteroaryl/alkyl nitriles were converted into 3-amino enones or 1,3-diketones by reaction with 2-bromoethanones in the presence of zinc under Blaise reaction conditions. The commercially important product avobenzone was synthesized.

    12. 1,3-Dipolar Cycloaddition

      Unprotected Xylose-Derived Nitrone in Stereodivergent Synthesis of 4-Hydroxypiperidine Enantiomers: Weak Lewis Acid Induced Alteration of Stereochemistry in 1,3-Dipolar Cycloaddition (pages 1533–1540)

      Tomasz Rowicki, Maciej Malinowski, Maciej Gryszel, Karolina Czerwińska, Izabela Madura, Ewa Mironiuk-Puchalska, Mariola Koszytkowska-Stawińska and Wojciech Sas

      Article first published online: 22 JAN 2015 | DOI: 10.1002/ejoc.201403410

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      A one-pot, two-step synthesis of chiral 7-oxa-1-azabicyclo[2.2.1]heptane derivatives from unprotected D-xylose was achieved by an intramolecular 1,3-dipolar cycloaddition of the N-(γ-alkenyl)-substituted nitrone intermediate. The stereochemical course of the reaction was altered by the addition of an achiral Lewis acid. The bicyclic byproducts were used to prepare two new enantiomeric piperidine-type iminosugars.

    13. Energetic Materials

      4,4,8,8-Tetranitroadamantane-2,6-diyl Dinitrate: A High-Density Energetic Material (pages 1541–1547)

      Yifei Ling, Xiaoli Ren, Weipeng Lai and Jun Luo

      Article first published online: 22 JAN 2015 | DOI: 10.1002/ejoc.201403449

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      The novel high-performance energetic material 4,4,8,8-tetranitroadamantane-2,6-diyl dinitrate has been synthesized by the formylation of 1,5-cyclooctanedione followed by intramolecular aldol condensation to construct the adamantane skeleton.

    14. Porphyrinoids

      Regioselective Nucleophilic Aromatic Substitution Reaction of meso-Pentafluorophenyl-Substituted Porphyrinoids with Alcohols (pages 1548–1568)

      Hartwig R. A. Golf, Hans-Ulrich Reissig and Arno Wiehe

      Article first published online: 28 JAN 2015 | DOI: 10.1002/ejoc.201403503

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      Readily available meso-pentafluorophenyl-substituted porphyrins and corroles can be functionalized at the para position with alcohols in regioselective SNAr reactions to give high yields under optimized conditions. The method has been applied to steroids as well as enantiopure and highly fluorinated alcohols. With suitable protecting groups, functionalized, polar A3B porphyrins are accessible.

    15. Cross-Coupling

      Copper-Catalyzed Asymmetric Oxidative Cross-Coupling of 2-Naphthols with Aryl Methyl Ketones (pages 1569–1574)

      Tao Deng, Hongjun Wang and Chun Cai

      Article first published online: 22 JAN 2015 | DOI: 10.1002/ejoc.201403512

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      A copper-catalyzed asymmetric oxidative cross-coupling reaction of 2-naphthols with aryl methyl ketones is presented. This transformation provides an efficient route to various functionalized naphtho[2,1-b]furan-1(2H)-ones in an enantiomerically enriched manner with molecular oxygen in air as the oxidant.

    16. Sulfonamides from Sulfinates

      Iodine-Catalyzed Oxidative Amination of Sodium Sulfinates: A Convenient Approach to the Synthesis of Sulfonamides under Mild Conditions (pages 1575–1582)

      Chonchanok Buathongjan, Danupat Beukeaw and Sirilata Yotphan

      Article first published online: 23 JAN 2015 | DOI: 10.1002/ejoc.201403531

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      A convenient synthesis of sulfonamides from sodium sulfinates and amines in the presence of catalytic iodine and sodium percarbonate as oxidant is described. This reaction proceeds under mild conditions, tolerates a wide range of functionalities, and provides a series of sulfonamide products in moderate to good yields.

    17. Organochalcogen Compounds

      Nucleophilic Cyclization of o-Alkynylbenzamides Promoted by Iron(III) Chloride and Diorganyl Dichalcogenides: Synthesis of 4-Organochalcogenyl-1H-isochromen-1-imines (pages 1583–1590)

      Jose S. S. Neto, Davi F. Back and Gilson Zeni

      Article first published online: 27 JAN 2015 | DOI: 10.1002/ejoc.201403534

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      4-Organochalcogenyl-1H-isochromen-1-imines are prepared by treatment of o-alkynylbenzamides with a combination of iron salts and diorganyl dichalcogenides in an electrophile-promoted nucleophilic cyclization.

    18. Reductive Iodination

      One-Pot Preparation of Alkyl Iodides from Esters by Indium-Catalyzed Reductive Cleavage of a Carbon–Oxygen Bond (pages 1591–1595)

      Norio Sakai, Yohei Matsushita, Takeo Konakahara, Yohei Ogiwara and Keisuke Hirano

      Article first published online: 20 JAN 2015 | DOI: 10.1002/ejoc.201403539

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      Indium tribromide effectively catalyzed the reductive iodination of esters to produce the corresponding alkyl iodides. A range of aliphatic and aromatic esters underwent the reaction, as did ester moieties in polymers.

    19. Natural Products

      An Enantioselective Synthesis of (R)-5,6-Octadecadienoic Acid (pages 1596–1601)

      Qiong Yu and Shengming Ma

      Article first published online: 20 JAN 2015 | DOI: 10.1002/ejoc.201403588

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      The scalable total synthesis of naturally occurring (R)-5,6-octadecadienoic acid was carried out in 12 % overall yield with an enantiomeric excess (ee) value of 98 % by using TBS-protected (TBS = tert-butyldimethylsilyl) propargyl alcohol and n-dodecanal with (R)-α,α-diphenylprolinol as the chiral source.

    20. Alkyl Sulfinates

      Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs (pages 1602–1605)

      J. Armando Lujan-Montelongo, Angel Ojeda Estevez and Fraser F. Fleming

      Article first published online: 22 JAN 2015 | DOI: 10.1002/ejoc.201403615

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      Alkyl sulfinates function as formal nucleophiles in Mannich reactions. Dehydration of the resulting N-(sulfonylmethyl)formamides gives TosMIC [(tolylsulfonyl)methyl isocyanide] analogs in an efficient two-step synthesis. The strategy provides a rapid, general, and efficient synthesis of sulfonylmethyl isonitriles by formally reversing the usual role of alkyl sulfinates as electrophiles.

    21. Radical Reactions

      Copper-Catalysed Alkylarylation of Activated Alkenes Using AIBN and Beyond: An Access to Cyano-Containing Oxindoles (pages 1606–1612)

      Dong Zhou, Zi-Hao Li, Jie Li, Shu-Hua Li, Ming-Wei Wang, Xiao-Ling Luo, Guo-Liang Ding, Rui-Long Sheng, Mei-Jun Fu and Shi Tang

      Article first published online: 27 JAN 2015 | DOI: 10.1002/ejoc.201403499

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      A copper-catalysed oxidative radical alkylarylation of activated alkenes using azobisisobutyronitrileand related compounds has been developed. Oxindoles with primary, and tertiary nitrile moieties at the 3-position were synthesized efficiently by a cascade addition/C(sp2)–H cyclization process.

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