European Journal of Organic Chemistry

Cover image for Vol. 2011 Issue 4

February 2011

Volume 2011, Issue 4

Pages 635–812

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Reversible Aminal Formation: Controlling the Evaporation of Bioactive Volatiles by Dynamic Combinatorial/Covalent Chemistry (Eur. J. Org. Chem. 4/2011)

      Barbara Buchs (née Levrand), Guillaume Godin, Alain Trachsel, Jean-Yves de Saint Laumer, Jean-Marie Lehn and Andreas Herrmann

      Version of Record online: 24 JAN 2011 | DOI: 10.1002/ejoc.201190003

  2. Graphical Abstract

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

      Direct Nucleophilic SN1-Type Reactions of Alcohols (pages 647–666)

      Enrico Emer, Riccardo Sinisi, Montse Guiteras Capdevila, Diego Petruzziello, Francesco De Vincentiis and Pier Giorgio Cozzi

      Version of Record online: 29 DEC 2010 | DOI: 10.1002/ejoc.201001474

      Thumbnail image of graphical abstract

      In the cool of the pool! A catalytic amount of Brønsted and Lewis acids can be used in the direct nucleophilic SN1-type reactions of alcohols with various nucleophiles. Water is the byproduct of this useful reaction.

  5. Short Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Gold–Carbene Complex Catalysis

      Cyclization of 2-Alkynylallyl Alcohols to Highly Substituted Furans by Gold(I)–Carbene Complexes (pages 667–671)

      A. Stephen K. Hashmi, Tobias Häffner, Matthias Rudolph and Frank Rominger

      Version of Record online: 27 DEC 2010 | DOI: 10.1002/ejoc.201001479

      Thumbnail image of graphical abstract

      Easily accessible 2-alkynylallyl alcohols were transformed into highly substituted furans under very mild reaction conditions by the use of gold(I)–carbene catalysts. A broad range of substrates could be transformed in high yields and within short reaction times.

    2. Hydrogenation

      Scope and Selectivity of Heterogeneous Rh0-Catalyzed Tandem Dehydrocoupling/Hydrogenation Using Me2NH·BH3 as a Stoichiometric H2 Source (pages 672–675)

      Matthew E. Sloan, Anne Staubitz, Kajin Lee and Ian Manners

      Version of Record online: 27 DEC 2010 | DOI: 10.1002/ejoc.201001332

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      The use of dimethylamine–borane in a the presence of Rh0 has been shown to function as an efficient hydrogenation/reduction system for a variety of organic substrates. This system has been shown to be mild by comparison to other reduction systems with epoxide, halide and nitrile groups unaffected under the reaction conditions used.

    3. Trichloromethylation

      Highly Stereoselective Trichloromethylation of N-(tert-Butylsulfinyl)aldimines: Facile Synthesis of Chiral α-Trichloromethylamines (pages 676–679)

      Ya Li, Yunlv Cao, Jiaying Gu, Wei Wang, Han Wang, Tao Zheng and Zhihua Sun

      Version of Record online: 17 DEC 2010 | DOI: 10.1002/ejoc.201001495

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      The first stereoselective synthesis of α-trichloromethylamines is described byusing a nucleophilic trichloromethylation strategy. With tetrabutylammonium triphenyldifluorosilicate as the mediator, the trichloromethyl anion (CCl3) from TMSCCl3 can be transferred to N-(tert-butylsulfinyl)aldimines in excellent yields and with high diastereoselectivity (≥99:1 dr).

  6. Full Papers

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

      Reversible Aminal Formation: Controlling the Evaporation of Bioactive Volatiles by Dynamic Combinatorial/Covalent Chemistry (pages 681–695)

      Barbara Buchs (née Levrand), Guillaume Godin, Alain Trachsel, Jean-Yves de Saint Laumer, Jean-Marie Lehn and Andreas Herrmann

      Version of Record online: 28 DEC 2010 | DOI: 10.1002/ejoc.201001433

      Thumbnail image of graphical abstract

      The evaporation of bioactive volatiles that are emitted from flowers to attract insects and that are used as fragrances in our everyday life is limited in time. Dynamic mixtures obtained by reversible aminal formation of suitably designed diamines with volatile aldehydes prolong the perception of these compounds in functional perfumery.

    2. Asymmetric Total Synthesis

      First Stereoselective Total Synthesis and Biological Evaluation of Amphidinin B and Its Analogues (pages 696–706)

      Jhillu S. Yadav, A. Srinivas Reddy, Ch. Suresh Reddy, Basi V. Subba Reddy, Venkateshwarlu Saddanapu and Anthony Addlagatta

      Version of Record online: 14 DEC 2010 | DOI: 10.1002/ejoc.201001205

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      The first stereoselective synthesis of amphidinin B has been achieved following Sharpless asymmetric epoxidation, base-induced epoxide ring-opening, radical cyclization, diastereoselective reduction of the exo-cyclic double bond, one-pot allylation followed by debenzylation, Evans alkylation, Barbier allylation, enzymatic kinetic resolution, and Yamaguchi esterification.

    3. Self-Assembling Dyes

      Room-Temperature Columnar Liquid-Crystalline Perylene Imido-Diesters by a Homogeneous One-Pot Imidification–Esterification of Perylene-3,4,9,10-tetracarboxylic Dianhydride (pages 707–712)

      Julien Kelber, Harald Bock, Olivier Thiebaut, Eric Grelet and Heinz Langhals

      Version of Record online: 9 DEC 2010 | DOI: 10.1002/ejoc.201001346

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      Perylenetetracarboxylic monoimide-diesters were synthesized by an amine-efficient, one-pot procedure. Alkyl group exchange of the ester moieties leads, through the use of the monoimido-monoanhydride, to room-temperature hexagonal columnar liquid crystals with potential as self-assembling electron acceptors for organic electronics.

    4. Furanoid Sugar Synthons

      Exploitation of Furanoid 5-Azido-3-C-Branched-Chain Sugars Towards Highly Functionalized Nitrogen-Containing Carbohydrate Derivatives (pages 713–720)

      Nuno M. Xavier, Yves Queneau and Amélia P. Rauter

      Version of Record online: 17 DEC 2010 | DOI: 10.1002/ejoc.201001119

      Thumbnail image of graphical abstract

      The synthesis of imino sugar derivatives containing an α,β-unsaturated lactone or ketone functionality has been explored starting from easily prepared furanoid δ-azido α,β-unsaturated esters. An easy route to the 1,2-dihydropyridin-3-one system was devised involving five steps and giving 29 % overall yield.

    5. Polar Diels–Alder Reactions

      Comprehensive DFT Study on Site-, Regio-, and Stereoselectivity of Diels–Alder Reactions Leading to 5-Hydroxybenzofurans (pages 721–729)

      Romina Brasca, María N. Kneeteman, Pedro M. E. Mancini and Walter M. F. Fabian

      Version of Record online: 9 DEC 2010 | DOI: 10.1002/ejoc.201001196

      Thumbnail image of graphical abstract

      Some Diels–Alder reactions leading to 5-hydroxybenzofurans were studied at the B3LYP/6-31G(d) level of theory in benzene as solvent (SP/CPCM). DFT calculations on the transition structures were carried out for all the possible reaction channels (site, regio-, and stereoisomeric channels were included in this study). Additionally, a description of the complete domino processes was performed.

    6. Peptide–Heterocycle Chimera

      Peptide–Heterocycle Chimera: New Classes of More Drug-Like Peptidomimetics by Ligations of Peptide–Bis(electrophiles) with Various Bis(nucleophiles) (pages 730–739)

      Adeeb El-Dahshan, Samina Nazir, Ahsanullah, Farzana Latif Ansari and Jörg Rademann

      Version of Record online: 22 DEC 2010 | DOI: 10.1002/ejoc.201001206

      Thumbnail image of graphical abstract

      Various peptidyl-substituted bis(electrophiles) were generated through C-acylations of polymer-supported phosphorus ylides with standard Fmoc-amino acid building blocks. The peptidyl-bis(electrophiles) were further converted into novel combinations of drug-like heterocycles with peptides by a set of ligation reactions with bis(nucleophiles).

    7. Alkaloid Synthesis

      Construction of the 5,10b-Phenanthridine Skeleton Using [3+2]-Cycloaddition of a Non-Stabilized Azomethine Ylide: Total Synthesis of (±)-Maritidine and (±)-Crinine Alkaloids (pages 740–750)

      Ganesh Pandey, Nishant R. Gupta and Smita R. Gadre

      Version of Record online: 13 DEC 2010 | DOI: 10.1002/ejoc.201001263

      Thumbnail image of graphical abstract

      The synthesis features construction of the BD ring with concomitant installation of a quarternary and tertiary carbon in a single operation by employing intramolecular 1,3-dipolar cycloaddition of a non-stabilizedazomethine ylide. Oxo-maritidine and oxo-crinine were found to be advanced and efficient intermediates for the synthesis of natural products of this class.

    8. Phosphatidylserine Probes

      Synthesis of Trifunctional Phosphatidylserine Probes for Identification of Lipid-Binding Proteins (pages 751–758)

      Saibal Bandyopadhyay and Dennis Bong

      Version of Record online: 17 DEC 2010 | DOI: 10.1002/ejoc.201001264

      Thumbnail image of graphical abstract

      We have synthesized a set of phosphatidylserine (PS) lipid photoaffinity cross-linking probes for the identification of novel PS receptor proteins. The PS lipid probes havepotential impact in the areas of discovery biology, anti-inflammatory therapeutics, and cellular delivery.

    9. Pseudorotaxanes

      Synthesis and Complexation Studies between Trifluoromethylammonium Threads and Dibenzo[24]Crown-8 (pages 759–769)

      Carsten Johnsen, Paul C. Stein, Kent A. Nielsen, Andrew D. Bond and Jan O. Jeppesen

      Version of Record online: 17 DEC 2010 | DOI: 10.1002/ejoc.201001277

      Thumbnail image of graphical abstract

      A weak anticooperative effect is observed when a dibenzo-24-crown-8 (DB24C8) binds to a thread component (4-H2·2PF6) incorporating two bis-alkylammonium recognition elements.

    10. Click Chemistry

      Heterogeneous Catalytic Reactions “On Water” by Using Stable Polymeric Alkynylcopper(I) Pre-Catalysts: Alkyne/Azide Cycloaddition Reactions (pages 770–776)

      Benjamin R. Buckley, Sandra E. Dann, Harry Heaney and Emma C. Stubbs

      Version of Record online: 16 DEC 2010 | DOI: 10.1002/ejoc.201001326

      Thumbnail image of graphical abstract

      We have established that the copper(I) catalyst required in triazole click reactions carried out by using copper(II) salts results from the formation of small amounts of polymeric alkynylcopper(I) ladder complexes. We have shown that polymeric alkynylcopper(I) ladder complexes can be used as effective heterogeneous pre-catalysts in “on water” triazole click reactions with loadings as low as 1 mol-%. These pre-catalysts can also be used in the corresponding iodo click reaction.

    11. Uracil Tautomers

      Mechanism of the Isotopic Exchange Reaction of the 5-H Hydrogen of Uracil Derivatives in Water and Nonprotic Solvents (pages 777–785)

      Martin Dračínský, Petr Jansa, Jana Chocholoušová, Jaroslav Vacek, Soňa Kovačková and Antonín Holý

      Version of Record online: 9 DEC 2010 | DOI: 10.1002/ejoc.201001335

      Thumbnail image of graphical abstract

      The mechanism of the isotopic exchange reaction of the 5-H hydrogen of uracil and other pyrimidine derivatives has been studied by NMR spectroscopy and DFT calculations. The key intermediate of the reaction is a C-5 tautomer in which the carbon atom at the 5-position has two hydrogen atoms.

    12. Asymmetric Catalysis

      Synthesis and Application of Diphenyl Sulfide Linked Bis(imidazoline) Ligands: Dramatic Electronic Effect of Ligands on Catalytic Behavior (pages 786–793)

      Xian Du, Han Liu and Da-Ming Du

      Version of Record online: 9 DEC 2010 | DOI: 10.1002/ejoc.201001347

      Thumbnail image of graphical abstract

      Diphenyl sulfide linked bis(imidazoline) ligands were synthesized. The electronic effects of the ligands were tuned rationally, and dramatic variation in their catalytic behavior was observed. N-Alkyl and N-H ligands showed much higher catalytic activity and improved enantioselectivity over N-Ts ligands in Pd-catalyzed asymmetric allylic alkylation reactions.

    13. Heterocyclic Synthesis

      Ring Expansion of 2-(1-Hydroxyalkyl)azetidines to 4-(2-Chloroethyl)oxazolidinones (pages 794–801)

      François Couty, Bruno Drouillat and Frédéric Lemée

      Version of Record online: 17 DEC 2010 | DOI: 10.1002/ejoc.201001375

      Thumbnail image of graphical abstract

      Ring expansion of 2-(1-hydroxyalkyl)azetidines provides functionalized oxazolidinones through a rapid and high yielding pathway. The scope of this ring expansion was studied in detail, and the nature of the byproducts obtained in some cases gave insight into the mechanism. Post functionalization of the 4-(2-chloroethyl)oxazolidinones was also examined.

    14. Natural Products

      Oxepinamides: Novel Liver X Receptor Agonists from Aspergillus puniceus (pages 802–807)

      Xin-Hua Lu, Qing-Wen Shi, Zhi-Hui Zheng, Ai-Bing Ke, Hua Zhang, Chang-Hong Huo, Ying Ma, Xiao Ren, Ye-Ying Li, Jie Lin, Qin Jiang, Yu-Cheng Gu and Hiromasa Kiyota

      Version of Record online: 13 DEC 2010 | DOI: 10.1002/ejoc.201000812

      Thumbnail image of graphical abstract

      Oxepinamides D–G, which are four novel oxepin-containing pyrimidines, were isolated from cultures of Aspergillus puniceus F02Z-1744. All four compounds showed moderate transcriptional activation on LXRα (Liver X Receptor), whereas no effects were observed on FXRα, PPARα, PPARβ, PPARγ, RARα, RXRα, or ERα at concentrations of 30 μM.

    15. Viburspiran, an Antifungal Member of the Octadride Class of Maleic Anhydride Natural Products (pages 808–812)

      Muhammad Saleem, Hidayat Hussain, Ishtiaq Ahmed, Siegfried Draeger, Barbara Schulz, Kathrin Meier, Michael Steinert, Gennaro Pescitelli, Tibor Kurtán, Ulrich Flörke and Karsten Krohn

      Version of Record online: 14 DEC 2010 | DOI: 10.1002/ejoc.201001324

      Thumbnail image of graphical abstract

      Viburspiran (8), the first representative of a new class of eight-membered maleicanhydride natural products, named octadrides, was isolated from the fungal endophyte Cryptosporiopsis sp. The structure was confirmed by single-crystal X-ray analysis and the absolute configuration established by TDDFT CD calculations. Viburspiran (8) exhibited antifungal activity against Botrytis cinerea and Microbotryum violaceum.

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