European Journal of Organic Chemistry

Cover image for Vol. 2014 Issue 1

January 2014

Volume 2014, Issue 1

Pages 5–253

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreview
    7. Short Communications
    8. Full Papers
    1. You have free access to this content
      Phenanthro-Annelated [5.5.6.6]- and (Broken) [6.5.6]Fenestranes (Eur. J. Org. Chem. 1/2014)

      Björn Bredenkötter, Beate Neumann, Hans-Georg Stammler and Dietmar Kuck

      Version of Record online: 18 DEC 2013 | DOI: 10.1002/ejoc.201390107

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      The cover picture shows the window-like structure of [5.5.6.6]fenestranes as an outlook onto the slopes of the Teutoburger Wald near Bielefeld, Germany. In an attempt to approach the – yet hypothetical – fully unsaturated tetrabenzo[5.5.5.5]fenestrene (“fenestrindene”, top left in the clouds), bearing a flattened tetracoordinate carbon atom, via a – likewise hypothetical – phenanthro-annellated [5.5.5.5]fenestrane (top right), two novel diastereomeric [5.5.6.6]fenestranes were synthesized: The all-cis-benzodiphenanthro[5.5.6.6.]fenestrane ketone (bottom left) and the corresponding cis,cis,trans,cis isomer (bottom right). The cyclization reactions giving rise to these complex fenestrane frameworks involve unexpected stereoselectivity and ring sizes, as discussed in the article by D. Kuck et al. on p. 53 ff.

  2. Editorial

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

      You have free access to this content
      EurJOC around the Clock (pages 5–6)

      Haymo Ross

      Version of Record online: 18 DEC 2013 | DOI: 10.1002/ejoc.201301748

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      This editorial reflects on the past year in EurJOC, including the launch of the EurJOC app, and looks forward at the changes to come in 2014.

  3. Graphical Abstract

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

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

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

      Helical-Chiral Small Molecules in Asymmetric Catalysis (pages 21–34)

      Maurice J. Narcis and Norito Takenaka

      Version of Record online: 2 DEC 2013 | DOI: 10.1002/ejoc.201301045

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      Molecular frameworks characterized by a space curve exhibit helical chirality. In this microreview we discuss a variety of synthetic strategies used to construct helical-chiral small molecules and highlight their beneficial effects as asymmetric catalysts.

  6. Short Communications

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

      Copper-Catalyzed Vinylsilane Allylation (pages 35–38)

      Loïc Cornelissen, Sébastien Vercruysse, Ayoub Sanhadji and Olivier Riant

      Version of Record online: 19 NOV 2013 | DOI: 10.1002/ejoc.201301360

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      Hereby is described a new copper-catalyzed vinylsilane transformation. Various vinylsilanes were allylated by using copper(I) salts, and this led to the formation of polysubstituted 1,4-dienes bearing sensitive moieties such as halogens, ketones, and aldehydes. TBAT = tetrabutylammonium difluorotriphenylsilicate.

    2. Ring-Opening/Ring-Closing Protocols from Nitrothiophenes: Easy Access to N-Fused Pyrroles through a Tandem 1,6-H Shift/6π-Electrocyclization (pages 39–43)

      Lara Bianchi, Massimo Maccagno, Giovanni Petrillo, Carlo Scapolla, Cinzia Tavani and Alessandra Tirocco

      Version of Record online: 21 NOV 2013 | DOI: 10.1002/ejoc.201301236

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      A pericyclic sequence followed by easy aromatization to the final pyrrole ring provides an appealing approach to functionalized N-fused pyrroles of preparative and, possibly, biological significance. Overall, starting from the ring opening of a nitrothiophene with amines, the process represents a further example of a highly carbon-economic ring-opening/ring-closing protocol.

    3. α-Amino-β-hydroxy Acids

      Synthesis of All the Diastereomers of 2-Amino-3-hydroxy-4,5-dimethylhexanoic Acid (pages 44–47)

      Jan Spengler and Fernando Albericio

      Version of Record online: 19 NOV 2013 | DOI: 10.1002/ejoc.201301257

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      The three stereocenters of 2-amino-3-hydroxy-4,5-dimethylhexanoic acid can be set up at will in a stepwise manner starting from Garner's aldehyde without the need for any additional chiral reagent. The synthesis involves reaction with 2-lithio-3-methyl-2-butene, followed by hydrogenation, intramolecular cyclization, Jones oxidation, and hydrolysis.

    4. Natural Product Synthesis

      Synthesis of the Pentacyclic Framework of the Alkaloid Tronocarpine (pages 48–52)

      Rubén O. Torres-Ochoa, Paul E. Reyes-Gutiérrez and Roberto Martínez

      Version of Record online: 22 NOV 2013 | DOI: 10.1002/ejoc.201301388

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      The synthesis of the pentacyclic framework of the indole alkaloid tronocarpine is described. For this purpose, N-tert-butoxycarbonyl (Boc)-protected tryptamine, a xanthate, and an unsaturated aldehyde are used. The synthesis involves radical oxidative aromatic substitution, double nucleophilic addition, and Ti-mediated Dieckmann cyclization; the desired product is obtained in an excellent overall yield.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreview
    7. Short Communications
    8. Full Papers
    1. Phenanthro-Annelated Fenestranes

      Phenanthro-Annelated [5.5.6.6]- and (Broken) [6.5.6]Fenestranes (pages 53–65)

      Björn Bredenkötter, Beate Neumann, Hans-Georg Stammler and Dietmar Kuck

      Version of Record online: 22 NOV 2013 | DOI: 10.1002/ejoc.201301382

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      The [5.5.6.6]fenestrane scaffold is accessible by twofold cyclodehydration starting by stereocontrolled spiro-Michael addition of 1,3-indanedione (1) to di(9-phenanthrylmethylidene)acetone (2). The all-cis (3) and the cis,cis,trans,cis isomer (4) can be obtained. Cyclodehydration of 2-(9-phenanthrylmethyl)-1,3-indanediols generates six-membered along with, or even instead of, five-membered rings.

    2. Nitrogen Heterocycle Synthesis

      A Short Asymmetric Synthesis of Octahydroindole Derivatives by Application of Catalytic C(sp3)–H Amination Reaction (pages 66–79)

      Marie Mazurais, Camille Lescot, Pascal Retailleau and Philippe Dauban

      Version of Record online: 15 OCT 2013 | DOI: 10.1002/ejoc.201301174

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      The short stereoselective synthesis of octahydroindole derivatives is reported. Catalytic asymmetric C(sp3)–H amination reactions and stereoselective intramolecular cycloaddition reactions are the key steps of the strategy that affords an efficient versatile access to molecular diversity.

    3. Ion-Pair Recognition

      The Synergetic Interplay of Weak Interactions in the Ion-Pair Recognition of Quaternary and Diquaternary Ammonium Salts by Halogenated Resorcinarenes (pages 80–85)

      N. Kodiah Beyeh, Melanie Göth, Lena Kaufmann, Christoph A. Schalley and Kari Rissanen

      Version of Record online: 21 OCT 2013 | DOI: 10.1002/ejoc.201300886

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      The noncovalent interactions of upper-rim halogenated resorcinarenes with quaternary and diquaternary ammonium salts were analysed in the gas phase and in solution. Enhanced ion pair binding by a synergetic combination of cation···π and hydrogen-bond interactions was observed in solution, while the electronic effects of the substituents prevailed in the gas phase in the absence of the counteranion.

    4. Wittig Reactions

      Investigations on the Operation of Stereochemical Drift in the Wittig Reaction by NMR and Variable-Temperature NMR Spectroscopy of Oxaphosphetane Intermediates and Their Quench Products (pages 86–98)

      Peter A. Byrne, Jimmy Muldoon, Yannick Ortin, Helge Müller-Bunz and Declan G. Gilheany

      Version of Record online: 22 NOV 2013 | DOI: 10.1002/ejoc.201301103

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      Stereochemical drift, previously only identified in a handful of isolated examples, is confirmed by variable-temperature NMR (VTNMR) spectroscopy as a general phenomenon in Wittig reactions of phosphonium ethylides with aromatic aldehydes. However, reactions of structurally related longer-chain alkylides are irreversible. The NMR methods used are described in full.

    5. Natural Product Synthesis

      Synthesis of (+)-O-Methylthalibrine by Employing a Stereocontrolled Bischler–Napieralski Reaction and an Electrochemically Generated Diaryl Ether (pages 99–104)

      Yuki Kawabata, Yu Naito, Tsuyoshi Saitoh, Kohei Kawa, Toshio Fuchigami and Shigeru Nishiyama

      Version of Record online: 13 NOV 2013 | DOI: 10.1002/ejoc.201301128

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      (+)-O-Methylthalibrine, a bis(benzylisoquinoline) alkaloid from the roots of the genus Thalictrum, has successfully been synthesized through the electrochemical construction of its diaryl ether core and simultaneous introduction of its two stereogenic centers.

    6. Host-Guest Systems

      Atropisomerization in Confined Space; Cucurbiturils as Tools to Determine the Torsional Barrier of Substituted Biphenyls (pages 105–110)

      Roymon Joseph and Eric Masson

      Version of Record online: 13 NOV 2013 | DOI: 10.1002/ejoc.201301460

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      Cucurbiturils were used for the first time as analytical accessories to access coveted kinetic parameters, namely the torsional barriers of substituted biphenyls.

    7. Asymmetric Synthesis

      Chemoenzymatic Synthesis of Enantiomerically Pure syn-Configured 1-Aryl-3-methylisochroman Derivatives (pages 111–121)

      Robert C. Simon, Eduardo Busto, Nina Richter, Ferdinand Belaj and Wolfgang Kroutil

      Version of Record online: 25 NOV 2013 | DOI: 10.1002/ejoc.201301429

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      A two-step sequence involving a biocatalytic hydrogen-transfer reduction and a syn-diastereoselective oxa-Pictet–Spengler reaction was established to provide a series of 1-aryl-3-methylchroman derivatives with perfect enantioselectivity; PTSA = para-toluenesulfonic acid.

    8. Total Synthesis

      Synthesis and Biological Evaluation of 7-Deoxy Analogues of the Human Rhinovirus 3C Protease Inhibitor Thysanone (pages 122–128)

      Katrin Schünemann, Daniel P. Furkert, Stephen Connelly, John D. Fraser, Jonathan Sperry and Margaret A. Brimble

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/ejoc.201301515

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      Several 7-deoxy analogues of the 3C protease inhibitor thysanone have been synthesised by using an oxa-Pictet–Spengler reaction as the key step. The biological activity of these compounds was also evaluated against human rhinovirus (HRV) 3C protease, the results of which suggest that inhibition of the enzyme requires the presence of the 7-oxa functionality.

    9. Thioamide Chemistry

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      Synthetic Studies Towards the Core Structure of Nakadomarin A by a Thioamide-Based Strategy (pages 129–139)

      Jai K. Chavda, Panayiotis A. Procopiou, Peter N. Horton, Simon J. Coles and Michael J. Porter

      Version of Record online: 14 NOV 2013 | DOI: 10.1002/ejoc.201301063

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      Two key steps in a projected total synthesis of nakadomarin A have been realised by using the unique chemistry of thioamides. Formation of the carbocyclic B ring can be effected by nucleophilic attack of a furan on a thiolactam-derived iminium ion, and the key quaternary centre can be established by a novel three-component coupling reaction.

    10. Asymmetric Hydrogenation

      Iridium Catalysts with Chiral Bicyclic Pyridine–Phosphane Ligands for the Asymmetric Hydrogenation of Olefins (pages 140–146)

      Xu Quan, Vijay Singh Parihar, Milan Bera and Pher G. Andersson

      Version of Record online: 17 OCT 2013 | DOI: 10.1002/ejoc.201301141

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      New pyridine-derived N,P-chelated iridium catalysts were prepared and evaluated in the asymmetric hydrogenation of trisubstituted olefins. High conversions and enantioselectivities were obtained.

    11. Supramolecular Assemblies

      Spin-Labelled Pillar[5]arene as Paramagnetic Host for Supramolecular Assemblies (pages 147–151)

      Roberta Manoni, Paolo Neviani, Paola Franchi, Elisabetta Mezzina and Marco Lucarini

      Version of Record online: 19 NOV 2013 | DOI: 10.1002/ejoc.201301153

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      The first example of a paramagnetic pillar[5]arene is reported.

    12. Organocatalysis

      Enantioselective Organocatalytic Synthesis of α-Cyclopropylphosphonates through a Domino Michael Addition/Intramolecular Alkylation Reaction (pages 152–163)

      Ana Maria Faísca Phillips and Maria Teresa Barros

      Version of Record online: 25 NOV 2013 | DOI: 10.1002/ejoc.201301207

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      α-Cyclopropylphosphonates with three stereogenic centres were obtained in good yields and high enantio- and diastereocontrol through a “one-pot” domino process catalysed by a chiral pyrrolidine. The highly functionalised cyclopropanes should be versatile starting materials for biologically important compounds.

    13. One-Pot C–C Coupling

      Direct One-Pot Synthesis of Naphthoxindoles from 4-Bromooxindoles by Suzuki–Miyaura Coupling and Aldol Condensation Reactions (pages 164–170)

      Kyeong-Yong Park, Bum Tae Kim and Jung-Nyoung Heo

      Version of Record online: 12 NOV 2013 | DOI: 10.1002/ejoc.201301242

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      Naphthoxindoles were synthesized in high to excellent yields through a reaction between 4-bromooxindoles and 2-formylphenylboronic acids under microwave irradiation. The one-pot reaction proceeds through a Suzuki–Miyaura coupling followed by an aldol-type condensation reaction.

    14. Small Ring Systems

      Titanium-Mediated Addition of Grignard Reagents to Acyl Cyanohydrins: Aminocyclopropane versus 1,4-Diketone Formation (pages 171–180)

      Paul Setzer, Gwénaël Forcher, Fabien Boeda, Morwenna S. M. Pearson-Long and Philippe Bertus

      Version of Record online: 29 OCT 2013 | DOI: 10.1002/ejoc.201301251

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      The 1,2-dianion reactivity of the reagent generated from EtMgBr and Ti(OiPr)4 was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples). When the reaction was performed in diethyl ether, 1,4-diketones were mainly isolated. Under certain conditions, cyclopropane derivatives were also obtained in good yields. A mechanism rationalizing this dichotomy is presented.

    15. Hydroxy-Directed Cyclopropanation of Esters: Synthesis of Trisubstituted Cyclopropanols (pages 181–187)

      Dmitry Astashko, Jin Kun Cha, Nagavaram Narsimha Rao and Bibhuti Bhusan Parida

      Version of Record online: 29 OCT 2013 | DOI: 10.1002/ejoc.201301252

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      A general route to sterically demanding 1,2,3-trisubstituted cyclopropanols has been devised by the Kulinkovich cyclopropanation of esters with disubstituted homoallylic alcohols. Generation in situ of a temporary alkoxy tether from a homoallylic alcohol overrides the otherwise unfavorable steric factors.

    16. Organocatalysis

      Thiophostone-Derived Brønsted Acids in the Organocatalyzed Transfer Hydrogenation of Quinolines: Influence of the P-Stereogenicity (pages 188–193)

      Angélique Ferry, Jérémy Stemper, Angela Marinetti, Arnaud Voituriez and Xavier Guinchard

      Version of Record online: 24 OCT 2013 | DOI: 10.1002/ejoc.201301253

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      The synthesis and catalytic activities of P-chiral Brønsted acids possessing a thiophostone-derived skeleton are described. The stereochemical outcome of the test reaction is strongly dependant on the stereochemistry of the phosphorus atom.

    17. Small Ring Systems

      Silver(I)-Mediated Dual Cleavage of C–C and C–O Bonds in the Reaction of Diarylmethylenecyclopropanes with Tetrahydrofuran: Synthesis of 4-(3-Halobut-3-enyloxy)butyl 2,2,2-Trifluoroacetate Derivatives (pages 194–197)

      Gen-Qiang Chen, Xiang-Ying Tang and Min Shi

      Version of Record online: 22 NOV 2013 | DOI: 10.1002/ejoc.201301262

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      Novel 4-(3-halobut-3-enyloxy)butyl 2,2,2-trifluoroacetate derivatives can be synthesized by AgI-mediated reactions of arylmethylenecyclopropanes with tetrahydrofuran at room temperature through dual cleavage of C–C and C–O bonds.

    18. Vinyl Ether Synthesis

      A Robust and General Protocol for the Lewis-Base-Catalysed Reaction of Alcohols and Alkyl Propiolates (pages 198–205)

      David Tejedor, Sergio J. Álvarez-Méndez, Juan M. López-Soria, Víctor S. Martín and Fernando García-Tellado

      Version of Record online: 31 OCT 2013 | DOI: 10.1002/ejoc.201301303

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      A practical protocol for the DABCO-catalysed synthesis of β-alkoxyacrylates is described. The protocol is efficient and economical, and it allows the transformation of a range of alcohols (including tertiary alcohols) into the corresponding β-alkoxyacrylate derivatives and the selective monoprotection of different diols (primary vs. secondary and tertiary).

    19. Self-Assembly

      Self-Sorting Effects in the Self-Assembly of Metallosupramolecular Rhombi from Chiral BINOL-Derived Bis(pyridine) Ligands (pages 206–216)

      Christoph Gütz, Rainer Hovorka, Caroline Stobe, Niklas Struch, Filip Topić, Gregor Schnakenburg, Kari Rissanen and Arne Lützen

      Version of Record online: 4 NOV 2013 | DOI: 10.1002/ejoc.201301314

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      Self-assembly of racemic bis(4-pyridyl) ligands based on a 1,1′-binaphthyl scaffold leads to dinuclear metallosupramolecular rhombi. Whereas 6,6′-substituted derivatives do not show any self-sorting, giving rise to a statistical mixture of stereoisomers, their 3,3′-difunctionalised isomers self-sort in a preferred social self-discrimination or in a highly selective self-recognition manner.

    20. Trifluoromethylthiolation

      Facile Assembly of 1-[(Trifluoromethyl)thio]isoquinolines through Reaction of 2-Alkynylbenzaldoxime with Silver (Trifluoromethyl)thiolate (pages 217–221)

      Qing Xiao, Jie Sheng, Qiuping Ding and Jie Wu

      Version of Record online: 26 NOV 2013 | DOI: 10.1002/ejoc.201301401

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      The title isoquinolines can be assembled through silver(I)-catalyzed reaction of 2-alkynylbenzaldoxime with silver (trifluoromethyl)thiolate in the presence of p-methoxybenzenesulfonyl chloride.

    21. Carbonylation

      Palladium-Catalyzed Carbonylative Transformations of Bromhexine into Bioactive Compounds as Glucocerebrosidase Inhibitors (pages 222–230)

      Muhammad Sharif, Anahit Pews-Davtyan, Jan Lukas, Johannes Schranck, Peter Langer, Arndt Rolfs and Matthias Beller

      Version of Record online: 6 NOV 2013 | DOI: 10.1002/ejoc.201301180

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      The first palladium-catalyzed carbonylative Suzuki–Miyaura arylations as well as alkoxy- and aminocarbonylations of the parent drug bromhexine were successfully performed. Some of the resulting new carbonylated products showed significant inhibition towards the glucocerebrosidase enzyme.

    22. Nucleoside Analogues

      A Convenient Route for the Synthesis of 3-Deazaspongosine (pages 231–236)

      Omprakash Bande and Piet Herdewijn

      Version of Record online: 22 NOV 2013 | DOI: 10.1002/ejoc.201301283

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      The synthesis of 3-deazaspongosine by the stereoselective glycosylation of imidazo[4,5-c]pyridine with tetraacetate-protected ribofuranose is described. The key step is the synthesis of the nucleobase starting from 2,6-dimethoxy-3-nitropyridin-4-amine by introducing the required functional groups at the 2 and 6 positions through the regioselective addition of allyl alcohol.

    23. Natural Product Synthesis

      Late-Stage β-Epimerization. A Stereodivergent to Stereoconvergent Relay to the First Total Synthesis of (+)-Murolic Acid (pages 237–243)

      Rodney A. Fernandes, Pradnya H. Patil and Asim K. Chowdhury

      Version of Record online: 28 NOV 2013 | DOI: 10.1002/ejoc.201301287

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      The first total synthesis of (+)-murolic acid is accomplished in 17 steps from ester 9 in 14.8 % overall yield. The key steps involve asymmetric dihydroxylation, orthoester Johnson–Claisen rearrangement and α-methylenation using Stiles reagent. A beneficial late-stage β-epimerization increased the efficiency of the synthesis.

    24. Carbohydrate Chemistry

      Asymmetric Synthesis of cis- and trans-2-Aryl-6-methylpyrans from D-Glucose by Arylation and Inversion of Configuration at the C-2 Position (pages 244–253)

      Kyosuke Michigami, Atsuko Shimazaki and Masahiko Hayashi

      Version of Record online: 15 NOV 2013 | DOI: 10.1002/ejoc.201301376

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      2-Aryl-3-hydroxy-6-(hydroxymethyl)pyrans were synthesized from tetra-O-acetyl-D-glucopyranosyl bromide by Friedel–Crafts arylation. The pyrans were converted into optically active cis- and trans-2-aryl-6-methylpyrans. Treatment of the pyrans with trimethylsilyl chloride and sodium iodide gave cis-analogues by deoxygenation at the C-3 position and inversion of configuration at the C-2 position

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