European Journal of Organic Chemistry

Cover image for Vol. 2014 Issue 25

September 2014

Volume 2014, Issue 25

Pages 5383–5609

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Full Papers
    1. You have free access to this content
      Diazocines on Molecular Platforms (Eur. J. Org. Chem. 25/2014)

      Tobias Tellkamp, Jun Shen, Yoshio Okamoto and Rainer Herges

      Article first published online: 26 AUG 2014 | DOI: 10.1002/ejoc.201490069

      Thumbnail image of graphical abstract

      The cover picture shows an artistic view of paramecia with artificial cilia. Cilia were probably the first strategy towards directed motion in evolutionary biology, emerging more than a billion years ago. Tremendous developments in dynamic supramolecular chemistry notwithstanding, artificial cilia are still elusive. Chiral, unidirectional molecular switches mounted on surfaces are the prerequisite for inducing cilia-driven directed motion. The article by R. Herges et al. on p. 5456 ff outlines how simple azobenzenes are transformed into chiral switches equipped with a molecular platform to mount them on gold surfaces.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Full Papers
    1. Graphical Abstract: Eur. J. Org. Chem. 25/2014 (pages 5383–5389)

      Article first published online: 26 AUG 2014 | DOI: 10.1002/ejoc.201490071

  3. News

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

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Full Papers
    1. Lithiated Small Heterocycles

      Complexation Phenomena and Dynamics at Work in the Lithiation Reactions of Small-Ring Heterocycles: Regio- and Stereoselectivity (pages 5397–5417)

      Vito Capriati, Saverio Florio and Renzo Luisi

      Article first published online: 5 AUG 2014 | DOI: 10.1002/ejoc.201402744

      Thumbnail image of graphical abstract

      This Microreview focuses on the regio- and stereoselective preparation of α- and ortho-lithiated oxiranes, aziridines, oxetanes, azetidines, and tetrahydrofurans with special emphasis on factors such as carbene-like character, aggregation, complexation phenomena and dynamics which strongly influence their applications to synthetic chemistry. Recent selected examples extracted from the literature are critically analysed and commented.

  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Full Papers
    1. Iminosugars

      Polyhydroxyamino-Piperidine-Type Iminosugars and Pipecolic Acid Analogues from a D-Mannose-Derived Aldehyde (pages 5419–5432)

      Camilla Matassini, Stefania Mirabella, Xhenti Ferhati, Cristina Faggi, Inmaculada Robina, Andrea Goti, Elena Moreno-Clavijo, Antonio J. Moreno-Vargas and Francesca Cardona

      Article first published online: 27 MAY 2014 | DOI: 10.1002/ejoc.201402427

      Thumbnail image of graphical abstract

      The synthesis of diversely substituted polyhydroxypiperidines, polyhydroxyaminopiperidines, and trihydroxypipecolic acid derivatives is reported, using Strecker reactions and double reductive aminations, starting from a D-mannose-derived aldehyde.

    2. Nitrogen Heterocycles

      α-Acryloylamidoalkyl Sulfones in a Synthetic Approach for the Preparation of 6-Alkyltetrahydropyridin-2-ones (pages 5433–5441)

      Nicola Lucchetti, Stefano Lancianesi and Marino Petrini

      Article first published online: 23 APR 2014 | DOI: 10.1002/ejoc.201402116

      Thumbnail image of graphical abstract

      The reaction of allylzinc bromides with α-acryloylamidoalkyl sulfones provides straightforward access to the corresponding homoallylamines, which can undergo a ring-closing metathesis reaction to give 6-alkyltetrahydropyridin-2-ones. Homoallylamino derivatives that contain a branched terminal alkene moiety preferentially proceed in a cross-metathesis reaction to give N-substituted fumaramides.

    3. Nucleoside Analogues

      Synthesis and Biological Activity of Triazole-Appended N,O-Nucleosides (pages 5442–5447)

      Roberto Romeo, Salvatore V. Giofrè, Caterina Carnovale, Maria A. Chiacchio, Agata Campisi, Raffaella Mancuso, Santa Cirmi and Michele Navarra

      Article first published online: 15 MAY 2014 | DOI: 10.1002/ejoc.201402106

      Thumbnail image of graphical abstract

      1,2,3-Triazole-appended N,O-nucleosides have been synthesized by an approach combining a 1,3-dipolar cycloaddition and an alkyne–azide click chemistry reaction. The synthesized compounds showed antiproliferative activity against tumor cell lines. These nucleoside analogues could be promising scaffolds for the construction of new anticancer agents.

    4. 3-Hydroxypipecolic Acid

      A Short, Chemo-Enzymatic Synthesis of Both Enantiomers of trans-3-Hydroxy­pipecolic Acid (pages 5448–5455)

      Stefano Begliomini, Lorenzo Sernissi, Dina Scarpi and Ernesto G. Occhiato

      Article first published online: 16 JUN 2014 | DOI: 10.1002/ejoc.201402258

      Thumbnail image of graphical abstract

      The Suzuki–Miyaura cross-coupling reaction of a lactam-derived enol phosphate, followed by hydroboration/oxidation, is employed for the synthesis of a 2-heteroaryl-3-hydroxypiperidine whose enantiomers are separated by enzymatic kinetic resolution. Both enantiomers are then converted into the corresponding 3-hydroxypipecolic acids, thus obtained in 6 or 7 steps and 15–17 % overall yield.

    5. Surface Functionalization

      Diazocines on Molecular Platforms (pages 5456–5461)

      Tobias Tellkamp, Jun Shen, Yoshio Okamoto and Rainer Herges

      Article first published online: 24 JUN 2014 | DOI: 10.1002/ejoc.201402541

      Thumbnail image of graphical abstract

      A bridged diazocine has been synthesized whose switching direction is restricted to one side. The diazocine was mounted onto a molecular platform which is known to have a high affinity to gold Au(111) surfaces. Upon irradiation of the thermodynamically more stable cis configuration in solution with light of 385 nm the trans isomer is formed and with green light (530 nm) back-isomerization to the cis form is achieved.

    6. Cucurbitane Triterpenes

      Roseic Acid and Roseolactones A and B, Furan-Cucurbitane Triterpenes from Russula aurora and R. minutula (Basidiomycota) (pages 5462–5468)

      Marco Clericuzio, Giovanni Vidari, Claudio Cassino, Laura Legnani and Lucio Toma

      Article first published online: 18 JUL 2014 | DOI: 10.1002/ejoc.201402208

      Thumbnail image of graphical abstract

      The fruiting bodies of the gilled fungi Russula aurora and R. minutula give a coral pink colour with sulfo-vanillin (SV). We found that they synthesize a few triterpenes, belonging to the seco-cucurbitane series, a rare skeleton type. These compounds show the above reaction with SV on TLC. Assignment of the configurations of 2 and 3 required a thorough ab initio theoretical investigation.

    7. Domino Process

      Dual Catalysis in Domino N-Benzylation/Intramolecular C–H Arylation: Regio- and Chemoselective Synthesis of Annelated Nitrogen Heterocycles (pages 5469–5475)

      Joydev K. Laha, Neetu Dayal, Swati Singh and Rohan Bhimpuria

      Article first published online: 21 JUL 2014 | DOI: 10.1002/ejoc.201402395

      Thumbnail image of graphical abstract

      A regio- and chemoselective synthesis of fused nitrogen heterocycles is described that proceeds through a domino N-benzylation/C–H arylation reaction sequence. The dual catalysis of this domino process is supported by a mechanistic study.

    8. Spiroaminals

      Spiroaminals – Crystal Structure and Computational Investigation of Conformational Preferences and Tautomerization Reactions (pages 5476–5486)

      Claudia Loerbroks, Birte Böker, Jens Cordes, Anthony G. M. Barrett and Walter Thiel

      Article first published online: 21 JUL 2014 | DOI: 10.1002/ejoc.201402576

      Thumbnail image of graphical abstract

      A joint experimental and computational study reveals the driving forces in the equilibria of spiroaminals. Although thermodynamic and electronic factors such as the anomeric effect lower the energy of the spiroaminal form, steric repulsion in combination with kinetic barriers favor the amine/imine structure. DFT calculations elucidate the mechanism of tautomerization.

    9. Molecular Synthons

      2,5-Diamide-Substituted Five-Membered Heterocycles: Challenging Molecular Synthons (pages 5487–5500)

      Chiara Fabbro, Simone Armani, Laure-Elie Carloni, Federica De Leo, Johan Wouters and Davide Bonifazi

      Article first published online: 23 JUL 2014 | DOI: 10.1002/ejoc.201402654

      Thumbnail image of graphical abstract

      2,5-Diamide-substituted five-membered heterocycles could easily be prepared from the corresponding biscarboxylic acid precursors by means of a Curtius-type rearrangement.

    10. Heteroannulation

      Iron-Promoted Domino Annulation of α-Enolic Dithioesters with Ninhydrin under Solvent-Free Conditions: Chemoselective Direct Access to Indeno[1,2-b]thiophenes (pages 5501–5508)

      Suvajit Koley, Sushobhan Chowdhury, Tanmoy Chanda, B. Janaki Ramulu, Ganesh Chandra Nandi and Maya Shankar Singh

      Article first published online: 21 JUL 2014 | DOI: 10.1002/ejoc.201402276

      Thumbnail image of graphical abstract

      The chemoselective synthesis of indeno[1,2-b]thiophenes was developed through the annulation of α-enolic dithioesters with ninhydrin under solvent-free conditions. This domino reaction sequence is highlighted by the use of inexpensive FeCl3·6H2O, its operational simplicity, a short reaction time, its functional-group tolerance, and the concomitant formation of two bonds and one thiophene ring.

    11. Heterocycles

      Synthesis, Stability, and Photoreactivity of Diazirinyl-Substituted N-Heterocycles Based on Indole, Benzimidazole, and Imidazole (pages 5509–5520)

      Björn Raimer, Thomas Wartmann, Peter G. Jones and Thomas Lindel

      Article first published online: 22 JUL 2014 | DOI: 10.1002/ejoc.201402354

      Thumbnail image of graphical abstract

      Benzimidazole leads among N-heterocycles that carry a 2-diazirinyl unit with regard to accessibility and thermal stability. Care is required with the labile imidazole analog; and N-methylated 2-diazirinylindole was also not stable. The investigated 2-diazirines are singlet carbene sources, as confirmed by DFT calculations. Irradiation in the presence of phenol forms the O-, p-, and o-products.

    12. Regiospecific Synthesis

      Regiospecific Synthesis of 7-Hydroxyindoles from Pyrroles by Anionic Benzannulation (pages 5521–5531)

      Bidyut Kumar Dinda, Shyam Basak and Dipakranjan Mal

      Article first published online: 24 JUL 2014 | DOI: 10.1002/ejoc.201402486

      Thumbnail image of graphical abstract

      7-Hydroxyindoles have been regioselectively synthesized in good yields by implementation of anionic [4+2] cycloaddition reactions on 2,3-disusbtituted pyrroles. The methodology has also been applied to furan analogues for the synthesis of 7-hydroxybenzofurans.

    13. Asymmetric Catalysis

      Enantioselective Hydrosilylation of Ketones Catalyzed by a Readily Accessible N-Heterocyclic Carbene–Ir Complex at Room Temperature (pages 5532–5539)

      Kanako Shinohara, Shun Kawabata, Hanako Nakamura, Yoshiki Manabe and Satoshi Sakaguchi

      Article first published online: 23 JUL 2014 | DOI: 10.1002/ejoc.201402279

      Thumbnail image of graphical abstract

      Stable monodentate NHC–Ir complexes containing hydroxy-amide groups on the side-arm could be synthesized with ease from naturally occurring amino acids such as leucine. Using these complexes, asymmetric hydrosilylation of aryl ketones with diethoxymethylsilane under very mild and flexible conditions readily afforded optically active alcohols with good enantioselectivities (73–96 % ee).

    14. Bioactive Natural Products

      Eudesmane-Type Sesquiterpenes from Curcuma phaeocaulis and Their Inhibitory Activities on Nitric Oxide Production in RAW 264.7 Cells (pages 5540–5548)

      Yue Liu, Jianghao Ma, Ying Wang, Paul Owusu Donkor, Qin Li, Suyu Gao, Yaguang Hou, Yang Xu, Jianing Cui, Liqin Ding, Feng Zhao, Ning Kang, Lixia Chen and Feng Qiu

      Article first published online: 25 JUL 2014 | DOI: 10.1002/ejoc.201402465

      Thumbnail image of graphical abstract

      Eight new sesquiterpenes (phaeusmanes A–H), together with eighteen known analogues, were isolated from the rhizomes of Curcuma phaeocaulis. Their complete structures were elucidated by NMR, MS, and CD spectroscopy. The NO inhibitory effects of the isolates are presented. A possible biogenetic pathway for N-containing eudesmane-type sesquiterpene 8 is postulated.

    15. Stereoselective Synthesis

      Stereoselective Synthesis of Lignans of Three Structural Types from a Common Intermediate, Enantioselective Synthesis of (+)-Yangambin (pages 5549–5556)

      Majid Khalil Syed, Cian Murray and Mike Casey

      Article first published online: 21 JUL 2014 | DOI: 10.1002/ejoc.201402584

      Thumbnail image of graphical abstract

      Construction of a bis(phenylpropanoid) backbone through a one-pot conjugate addition/aldol reaction. Reduction and acid-catalysed cyclisation of the aldol intermediate gave (+)-yangambin in good yield with 2,5-diaryltetrahydrofuran lignans as minor products, whereas the acid-catalysed cyclisation of the aldol intermediate resulted in a derivative of the lignan lirionol.

    16. Chiral Pool Synthesis

      A Concise Synthesis of (2R,3R)- and (2R,3S)-3-Hydroxypipecolic Acids, and Total Synthesis of (–)-Deoxoprosopinine and (+)-2-epi-Deoxoprosopinine from D-Glycals (pages 5557–5563)

      Asadulla Mallick, Nitee Kumari, Rashmi Roy, Ashokkumar Palanivel and Yashwant D. Vankar

      Article first published online: 22 JUL 2014 | DOI: 10.1002/ejoc.201402603

      Thumbnail image of graphical abstract

      New syntheses of (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids, and total syntheses of (–)-deoxoprosopinine and (+)-2-epi-deoxoprosopinine are reported. The syntheses started from D-glycals, and Ferrier rearrangement, intramolecular cyclization, and Grignard reactions were key steps.

    17. Glycosylation

      Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O-Glycosylation of 1-O-Acetyl Sugars as Glycosyl Donors (pages 5564–5573)

      Rashmi Roy, Parasuraman Rajasekaran, Asadulla Mallick and Yashwant D. Vankar

      Article first published online: 24 JUL 2014 | DOI: 10.1002/ejoc.201402606

      Thumbnail image of graphical abstract

      The Ferrier rearrangement of glycals, and the glycosylation of 1-O-acetyl sugars using an AuCl3/phenylacetylene catalyst system are described. Relay catalysis was observed when phenylacetylene was used in combination with AuCl3. The efficient production of glycosides was achieved in shortened reaction times.

    18. Spiro Compounds

      Synthesis of the Spiroketal Fragment of (–)-Ushikulide A (pages 5574–5581)

      Jhillu S. Yadav, N. Mallikarjuna Reddy, Md. Ataur Rahman and Attaluri R. Prasad

      Article first published online: 21 JUL 2014 | DOI: 10.1002/ejoc.201402196

      Thumbnail image of graphical abstract

      The stereoselective synthesis of the spiroketal fragment of (–)-Ushikulide A is described. The key tetrahydropyran moiety was synthesized by using segment-coupled Prins cyclization of an α-acetoxy ether. Both iodohydrin derivatives were obtained from a common THP ring compound by reductive ring cleavage under Boord reaction conditions.

    19. Ring-Rearrangement Metathesis

      Diversity-Oriented Approach to Carbocycles and Heterocycles through Ring-Rearrangement Metathesis, Fischer Indole Cyclization, and Diels–Alder Reaction as Key Steps (pages 5582–5590)

      Sambasivarao Kotha and Ongolu Ravikumar

      Article first published online: 18 JUL 2014 | DOI: 10.1002/ejoc.201402273

      Thumbnail image of graphical abstract

      Dicyclopentadiene derivatives were subjected to ring-rearrangement metathesis to deliver a range of fused polycycle frameworks containing carbocycles, oxacycles, and azacycles. Here, Fischer indole cyclization and the Diels–Alder reaction are employed as key steps.

    20. Nonproteinogenic Amino Acids

      Biocatalytic Synthesis of Enantiopure β-Methoxy-β-arylalanine Derivatives (pages 5591–5597)

      Shiming Fan, Shouxin Liu, Hubo Zhang, Ying Liu, Yihuang Yang and Longyi Jin

      Article first published online: 21 JUL 2014 | DOI: 10.1002/ejoc.201402470

      Thumbnail image of graphical abstract

      Chiral β-hydroxy-β-arylalanine and β-methoxy-β-arylalanine derivatives were prepared stereoselectively from ethyl 3-oxo-3-arylpropanoates through oximation, hydrogenation, N-acetylation, methylation, and enzyme-catalyzed hydrolysis.

    21. Multicomponent Reactions

      A Three-Component Reaction for the Synthesis of Diverse, Densely Substituted 2′,3′-Dihydrospiro[indoline-3,6′-[1,3]oxazine]s (pages 5598–5602)

      Jing Zhang, Hong Gao, Jing Sun and Chao-Guo Yan

      Article first published online: 21 JUL 2014 | DOI: 10.1002/ejoc.201402500

      Thumbnail image of graphical abstract

      Three-component reactions of α,β-unsaturated N-arylaldimines, dialkyl acetylenedicarboxylate, and N-alkylisatins afforded 3′-aryl-2′-styryl-2′,3′-dihydrospiro[indoline-3,6′-[1,3]oxazine]s in good yields.

    22. Palladium Nanoparticles

      Pd Nanoparticles Immobilized on Nanosilica Triazine Dendritic Polymer: A Reusable Catalyst for the Synthesis of Mono-, Di-, and Trialkynylaromatics by Sonogashira Cross-Coupling in Water (pages 5603–5609)

      Amir Landarani Isfahani, Iraj Mohammadpoor-Baltork, Valiollah Mirkhani, Ahmad R. Khosropour, Majid Moghadam and Shahram Tangestaninejad

      Article first published online: 30 JUL 2014 | DOI: 10.1002/ejoc.201402503

      Thumbnail image of graphical abstract

      Palladium nanoparticles immobilized on nano-silica triazine dendritic polymer (Pdnp-nSTDP) was found to be a highly effective catalyst for the Sonogashira cross-coupling of aryl halides (iodides, bromides, and chlorides) with aromatic and aliphatic terminal alkynes. The reaction was best performed in water as a green solvent in the presence of just 0.01 mol-% of the catalyst at room temperature.

SEARCH

SEARCH BY CITATION