European Journal of Organic Chemistry

Cover image for Vol. 2014 Issue 33

November 2014

Volume 2014, Issue 33

Pages 7277–7504

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
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      High-Yielding Total Synthesis of Sexually Deceptive Chiloglottones and Antimicrobial Dialkylresorcinols through an Organocatalytic Reductive Coupling Reaction (Eur. J. Org. Chem. 33/2014)

      Rudrakshula Madhavachary and Dhevalapally B. Ramachary

      Article first published online: 12 NOV 2014 | DOI: 10.1002/ejoc.201490093

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      The cover picture shows how an organocatalytic reductive coupling reaction became a key reaction for the high-yielding two-pot total synthesis of sexually deceptive chiloglottones, regarded as an unexplored class of natural products. Chiloglottones 1–6 were identified in orchids of the genus Chiloglottis, in which they act as pheromones to fool its pollinator, the male wasp Neozeleboria cryptoides. Details are discussed in the Short Communication by R. Madhavachary and D. B. Ramachary on p. 7317 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    1. Graphical Abstract: Eur. J. Org. Chem. 33/2014 (pages 7277–7284)

      Article first published online: 12 NOV 2014 | DOI: 10.1002/ejoc.201490095

  3. News

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

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    1. Sugar-Derived Organocatalysts

      Applications of Carbohydrate-Based Organocatalysts in Enantioselective Synthesis (pages 7291–7303)

      Ana Maria Faísca Phillips

      Article first published online: 2 OCT 2014 | DOI: 10.1002/ejoc.201402689

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      Carbohydrates, with their rigid backbones, large numbers of functional groups and high contents of chiral centres, are an appealing natural resource for the development of organocatalysts. They are becoming increasingly popular new tools for enantioselective synthesis, and this subject is reviewed for the period from 2009 to mid-2014.

    2. Complementary Recognition Sites

      Supramolecular Control of Reactivity and Catalysis – Effective Molarities of Recognition-Mediated Bimolecular Reactions (pages 7304–7315)

      Stefano Di Stefano, Roberta Cacciapaglia and Luigi Mandolini

      Article first published online: 26 AUG 2014 | DOI: 10.1002/ejoc.201402690

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      Effective molarities (EM) of intramolecular reactions in 1:1 supramolecular complexes are critically surveyed and analyzed in terms of entropy and strain.

  5. Short Communications

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

      High-Yielding Total Synthesis of Sexually Deceptive Chiloglottones and Antimicrobial Dialkylresorcinols through an Organocatalytic Reductive Coupling Reaction (pages 7317–7323)

      Rudrakshula Madhavachary and Dhevalapally B. Ramachary

      Article first published online: 24 SEP 2014 | DOI: 10.1002/ejoc.201403128

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      Sexually deceptive chiloglottones, antimicrobial dialkylresorcinols, and their many analogues are synthesized in very good yields in a sequential two-pot manner by using an “organocatalytic reductive coupling reaction” as the key step.

    2. Trifluoromethylthiolation

      An Improved Protocol for the Synthesis of α-Trifluoromethylthio-Substituted Ketones by Copper-Mediated Trifluoromethylthiolation of α-Bromo Ketones (pages 7324–7328)

      Yangjie Huang, Xing He, Haohong Li and Zhiqiang Weng

      Article first published online: 19 OCT 2014 | DOI: 10.1002/ejoc.201403221

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      An improved protocol for the copper-mediated trifluoromethylthiolation of α-bromo ketones by using (bpy)Cu(SCF3) (bpy = 2,2′-bipyridyl) to afford the corresponding α-trifluoromethylthio-substituted ketones in good to excellent yields is presented. The procedure tolerates electron-withdrawing and electron-donating groups on the aromatic rings.

    3. Kinetics

      Unusual Reaction Constant for Hydride Transfer from a Carbanion to 9-Arylxanthyliums (pages 7329–7332)

      Fengrui Liu and Xiaoqing Zhu

      Article first published online: 15 OCT 2014 | DOI: 10.1002/ejoc.201403023

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      An unusual reaction constant obtained from the kinetics for hydride transfer from a carbanion to 9-arylxanthyliums is obtained. The results are in contrast to thermodynamics analysis results for simple hydride-transfer reactions and indicate that this reaction is no longer a simple hydride-transfer reaction. An “intermediate” is also found during the reaction, and a possible structure is proposed.

    4. Conjugated Chirons

      Transformation of Glycals into α,β,γ,δ-Conjugated Chirons under Metal-Free Conditions (pages 7333–7338)

      Tatina Madhubabu, Syed Khalid Yousuf, Anil Kumar Kusunuru and Debaraj Mukherjee

      Article first published online: 19 OCT 2014 | DOI: 10.1002/ejoc.201403041

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      A diastereoselective, metal-free, one-pot domino synthetic strategy is developed for the transformation of glycals into new chiral scaffolds. Optimization of the reaction conditions to exclude normal Ferrier products, characterization of the new entities, and a plausible mechanism are presented (TMSOTf: trimethylsilyl trifluoromethanesulfonate).

    5. Organocatalysis

      Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation (pages 7339–7342)

      Pedro C. Barrulas, Andrea Genoni, Maurizio Benaglia and Anthony J. Burke

      Article first published online: 15 OCT 2014 | DOI: 10.1002/ejoc.201403180

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      Cinchona derivatives for the successful enantioselective addition of trichlorosilane to ketimines are developed. Excellent yields with good to high enantioselectivities (up to 91 %) are obtained in the reduction of differently substituted substrates. Remarkably high turnover frequencies for imine hydrosilylation are observed at a catalyst loading of only 1 mol-%.

    6. C–H Activation

      Functionalization of the Benzylic C–H Bonds in Azaarenes by Cobalt-Catalyzed 1,4-Addition to Enones (pages 7343–7346)

      Zaini Jamal, Yong-Chua Teo and Ling-Keong Wong

      Article first published online: 15 OCT 2014 | DOI: 10.1002/ejoc.201403203

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      Functionalization of the C(sp3)–H bonds in azaarenes catalyzed by CoCl2 as an inexpensive Lewis acid catalyst is reported. Enones are demonstrated to be good C=C electrophilic acceptors for the construction of various azaarene-containing 1,4-addition products in yields up to 95 %.

    7. Transfer Hydrogenation

      Photodriven Transfer Hydrogenation of Olefins (pages 7347–7352)

      Dasheng Leow, Ying-Ho Chen, Tzu-Hang Hung, Ying Su and Yi-Zhen Lin

      Article first published online: 15 OCT 2014 | DOI: 10.1002/ejoc.201403021

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      An improved practical method for the photodriven diimide reduction of olefins is reported. This catalyst-free procedure proceeds at ambient temperature, utilizes air as the oxidant and a lower hydrazine loading, and produces inert nitrogen gas as the sole byproduct. Several functional groups are tolerated and the reaction can be chemoselective. CFL = compact fluorescent light.

  6. Full Papers

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

      Chiroptical Signatures of Planar and Central Chirality in [2]Paracyclo[2](5,8)quinolinophane Derivatives (pages 7353–7363)

      Giuseppe Mazzeo, Giovanna Longhi, Sergio Abbate, Federica Buonerba and Renzo Ruzziconi

      Article first published online: 14 OCT 2014 | DOI: 10.1002/ejoc.201402945

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      Quinolinophane derivatives possessing both planar and central chirality are investigated by experimental and computational chiroptical methods. Vibrational circular dichroism defines unequivocally planar chirality and optical rotation measurements provide an excellent indication of central chirality.

    2. Addition Reactions

      Toward Bis C,C-Glycosyl Compounds and Anomeric γ-Glycoamino Acids through Michael Addition Reaction of Nitromethane on Z/E Push-Pull Sugar Olefins (pages 7364–7376)

      Mylène Richard, Anne-Sophie Felten, Claude Didierjean, Manuel Ruiz-Lopez, Yves Chapleur and Nadia Pellegrini-Moïse

      Article first published online: 8 OCT 2014 | DOI: 10.1002/ejoc.201402958

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      The Michael addition reaction of a nitronate anion at the anomeric center of push-pull sugar olefins gave a new and efficient access to bis C,C-glycosyl compounds that could be converted into optically pure anomeric γ-amino acids. A strong difference in the reactivity of the E and Z isomers of the exo-glycals was observed and was rationalized by quantum chemical calculations.

    3. Quinones

      Reactions of p-Quinols with Aldehydes and Imines: Stereoselective Access to Polyheterobicyclic and Tricyclic Systems (pages 7377–7388)

      Carolina García-García, María C. Redondo, María Ribagorda and M. Carmen Carreño

      Article first published online: 6 OCT 2014 | DOI: 10.1002/ejoc.201403114

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      Base-promoted reactions of p-quinols with aldehydes or sulfonyl imines enable direct access to dihydrobenzo[d][1,3]dioxolone or tetrahydrobenzo[d]oxazolone skeletons. A stereoselective synthesis of tricyclic systems was achieved by using sulfonyl imine and DABCO/LiClO4 in THF through a domino sequence of 1,2-addition, intramolecular aza-Michael and aza-Diels–Alder reactions.

    4. Micelles

      Micellar Polyaromatic Capsules: Enhanced Emissive Properties through Shell-Functionalization (pages 7389–7394)

      Kei Kondo, Akira Suzuki, Munetaka Akita and Michito Yoshizawa

      Article first published online: 10 OCT 2014 | DOI: 10.1002/ejoc.201403136

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      Functionalization of the polyaromatic shell of a micelle-like molecular capsule was accomplished by simple functionalization of the amphiphilic subunits. The shell-functionalization drastically enhances the host and host–guest emissive properties.

    5. Ketone α-Arylation

      Di-tert-butylneopentylphosphine (DTBNpP): An Efficient Ligand in the Palladium-Catalyzed α-Arylation of Ketones (pages 7395–7404)

      Steven M. Raders, Jessica M. Jones, Jeffrey G. Semmes, Steven P. Kelley, Robin D. Rogers and Kevin H. Shaughnessy

      Article first published online: 10 OCT 2014 | DOI: 10.1002/ejoc.201402474

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      Ketone α-arylation with aryl bromides and chlorides using di-(tert-butyl)neopentylphosphine (DTBNpP) in combination with palladium is described. This catalyst system provides an efficient route to benzofurans through the condensation of 2-bromophenols with ketones.

    6. Catalytic C–N Coupling

      Concise Synthesis of Vesnarinone and Its Analogues by Using Pd-Catalyzed C–N Bond-Forming Reactions (pages 7405–7412)

      Yi Yang See, Tuan Thanh Dang, Anqi Chen and Abdul Majeed Seayad

      Article first published online: 14 OCT 2014 | DOI: 10.1002/ejoc.201403054

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      An efficient and concise synthesis of vesnarinone was achieved in three steps by using palladium-catalyzed C–N bond-forming reactions, which included the Buchwald–Hartwig amination and an aminocarbonylation reaction. High overall yields were obtained by using this strategy for the preparation of several vesnarinone analogues.

    7. Bridged-Ring Systems

      Synthesis of Quinuclidines by Intramolecular Silver-Catalysed Amine Additions to Alkynes (pages 7413–7425)

      Arjen C. Breman, Andrea Ruiz-Olalla, Jan H. van Maarseveen, Steen Ingemann and Henk Hiemstra

      Article first published online: 6 OCT 2014 | DOI: 10.1002/ejoc.201403099

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      We report the synthesis of (enantiomerically pure) 2-alkylidenequinuclidines by an intramolecular hydroamination reaction catalysed by silver triflate. After cyclization to the appropriate quinuclidines, the cinchona alkaloids dihydroquinidine and dihydroquinine were obtained in a two-step procedure.

    8. Cross-Coupling

      Synthesis of Soai Type 2-Arylpyrimidine-5-carbaldehydes through Desulfurative Cross-Coupling with Arylboronic Acids (pages 7426–7432)

      Oleg V. Maltsev, Rodger Rausch, Zheng-Jun Quan and Lukas Hintermann

      Article first published online: 8 OCT 2014 | DOI: 10.1002/ejoc.201403133

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      2-Arylpyrimidine-5-carbaldehydes, which are of relevance as substrates in Soai's asymmetric autocatalysis, are prepared through Liebeskind–Srogl coupling of aryl boronic acids with 2-methylthiopyrimidine-5-carbaldehyde; the latter is obtained in a hydrolytic condensation of two symmetric amidinium salts.

    9. Nitration

      Oxone®/KI-Mediated Nitration of Alkenes and Alkynes: Synthesis of Nitro- and β-Iodonitro-Substituted Alkenes (pages 7433–7442)

      Sornsiri Hlekhlai, Natthapol Samakkanad, Tassaporn Sawangphon, Manat Pohmakotr, Vichai Reutrakul, Darunee Soorukram, Thaworn Jaipetch and Chutima Kuhakarn

      Article first published online: 6 OCT 2014 | DOI: 10.1002/ejoc.201402750

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      Oxone® (2KHSO5·KHSO4·K2SO4) was used to promote the reactions of alkenes and alkynes with sodium nitrite (NaNO2) and potassium iodide (KI) to afford the corresponding nitro and β-iodonitro-substituted alkenes, respectively, in moderate to good yields.

    10. Heterocycle Synthesis

      Synthesis of 6-Substituted Phenanthridine Derivatives by Palladium-Catalysed Domino Suzuki–Miyaura/Aza-Michael Reactions (pages 7443–7450)

      Xiaobo Bao, Wei Yao, Qihua Zhu and Yungen Xu

      Article first published online: 8 OCT 2014 | DOI: 10.1002/ejoc.201402913

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      A domino reaction involving a palladium-catalysed Suzuki–Miyaura reaction followed by an intramolecular aza-Michael addition is presented. This allows the formation of a C–C bond and a C–N bond under mild conditions in one pot.

    11. Domino Reaction

      Iron-TEMPO-Catalyzed Domino Aerobic Alcohol Oxidation/Oxidative Cross-Dehydrogenative Coupling for the Synthesis of α-Keto Amides (pages 7451–7457)

      Surya Srinivas Kotha, Selvaraj Chandrasekar, Samrat Sahu and Govindasamy Sekar

      Article first published online: 9 OCT 2014 | DOI: 10.1002/ejoc.201402961

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      An iron-TEMPO-catalyzed (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxy), aerobic process was developed to synthesize α-keto amides. This reaction proceeds through a domino alcohol oxidation/oxidative cross-dehydrogenative coupling sequence and uses 2-hydroxyacetophenones and amines as the starting materials.

    12. Lewis Acid Catalysis

      Access to Polycyclic Derivatives by Triflate-Catalyzed Intramolecular Hydroarylation (pages 7458–7468)

      Bastien Cacciuttolo, Sophie Poulain-Martini, Fabien Fontaine-Vive, Mahmoud Ali Hussein Abdo, Hussein El-Kashef and Elisabet Duñach

      Article first published online: 13 OCT 2014 | DOI: 10.1002/ejoc.201402972

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      Nonactivated aromatic compounds bearing side-chain olefin substituents were cyclised into polycyclic compounds in good-to-excellent yields under In(OTf)3 (OTf = trifluoromethanesulfonate) and Bi(OTf)3 catalysis. This intramolecular cycloisomerisation leads to the synthesis of indane, tetralin or benzosuberan derivatives and allows sequential and tandem polycyclisations in one step.

    13. Polycyclic Structures

      Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl-Shaped Core (pages 7469–7480)

      Ehsan Ullah Mughal, Beate Neumann, Hans-Georg Stammler and Dietmar Kuck

      Article first published online: 6 OCT 2014 | DOI: 10.1002/ejoc.201402995

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      C3- and C1-symmetrical tribenzotriquinacene-based tris-tolanes were synthesized and found to be separable, in contrast to TBTQ trialdehydes, triacetylenes and triiodo precursors. Both 2,6,10- and 2,6,11-tris-tolanes were converted into the tris-pentaphenylphenyl-TBTQ hydrocarbons, as shown for the C3-isomer. Attempts to generate warped TBTQ-centered graphene cuttings from the C3 derivative failed.

    14. Arene Amination

      RhIII-Catalysed Hydrazine-Directed C(sp2)–H Amination of Phenidones with N-Alkyl-O-benzoyl-hydroxylamines (pages 7481–7488)

      Yu Xue, Zhoulong Fan, Xiaolong Jiang, Kui Wu, Meining Wang, Chunyong Ding, Qizheng Yao and Ao Zhang

      Article first published online: 9 OCT 2014 | DOI: 10.1002/ejoc.201402999

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      A RhIII-catalysed ortho C–H amination of phenidones under mild conditions at room temperature was developed using N-alkyl-O-benzoyl-hydroxylamines as aminating agents, and with a cyclic hydrazine moiety as a directing group, yields of up to 97 % and a high functional group tolerance were observed.

    15. Cyclic Rearrangement

      Facile Redox Interconversion of 6,11-Diphenyldibenzo[b,f][1,4]diazocine and 2-(2-Aminophenyl)-1,3-diphenylisoindole: Reversible SET Ring Contraction and Expansion Processes (pages 7489–7498)

      John J. Eisch, Wei Liu, Lisheng Zhu and Arnold L. Rheingold

      Article first published online: 14 OCT 2014 | DOI: 10.1002/ejoc.201403101

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      Our attempt to form the aromatic 6,11-diphenyldibenzo[b,f]5,12-dihydro[1,4]diazocine by treating 6,11-diphenyldibenzo[b,f][1,4]diazocine with Na and then water led instead to 2-(2-aminophenyl)-1,3-diphenylisoindole. Other reductants for this reaction were o-diaminobenzene (o-DAB), titanium(II) salts and HI; the reverse reaction was caused by O2 or DDQ.

    16. Carbocycle Synthesis

      Phase-Transfer-Catalyst-Mediated Domino Reaction of γ-Nitro Ketones with Chalcones: Approach to Functionalized Six-Membered-Ring Carbocycles (pages 7499–7504)

      Lu Yu, Qingjing Yang and Pengfei Li

      Article first published online: 6 OCT 2014 | DOI: 10.1002/ejoc.201403075

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      Domino reactions between γ-nitro ketones and α,β-unsaturated ketones using a phase-transfer catalyst were developed. In the presence of Bu4NI and KOH, functionalized six-membered-ring carbocycles were formed in good to high yields and with excellent diastereoselectivities. This represents a new and efficient method for the construction of functionalized cyclohexane skeletons.

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