European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 14

May 2015

Volume 2015, Issue 14

Pages 2983–3177

  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 and Absolute Configuration of Auriculamide, a Natural Product from the Predatory Bacterium Herpetosiphon aurantiacus (Eur. J. Org. Chem. 14/2015)

      Sebastian Schieferdecker, Nicole Domin, Christine Hoffmeier, Donald A. Bryant, Martin Roth and Markus Nett

      Article first published online: 5 MAY 2015 | DOI: 10.1002/ejoc.201590036

      Thumbnail image of graphical abstract

      The cover picture shows a genomic map of the predatory bacterium Herpetosiphon aurantiacus. Similar to a treasure map, M. Nett et al. used the genomic data to track the biosynthesis genes of the previously discovered natural product auriculamide. Details are discussed in their article on 3057 ff.

  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. Synthesis of Azaheterocycles

      Furan's Gambit: Electrophile-Attack-Triggered Sacrifice of Furan Rings for the Intramolecular Construction of Azaheterocycles (pages 2999–3016)

      Igor V. Trushkov, Maxim G. Uchuskin and Alexander V. Butin

      Article first published online: 3 FEB 2015 | DOI: 10.1002/ejoc.201403580

      Thumbnail image of graphical abstract

      Chemistry is like chess! A gambit is a chess opening in which a player sacrifices something to achieve something else. The concept of the gambit is also used in organic chemistry. This review deals with intramolecular transformations pertaining to the sacrifice of a furan ring for the production of a variety of nitrogen heterocycles.

  5. Short Communications

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

      4,8-Disubstituted Bicyclo[3.3.1]nona-2,6-dienes as Chiral Ligands for Rh-Catalyzed Asymmetric 1,4-Addition Reactions (pages 3017–3021)

      Renaldas Rimkus, Marius Jurgelėnas and Sigitas Stončius

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500202

      Thumbnail image of graphical abstract

      Chiral C2-symmetric 4,8-endo,endo-disubstituted bicyclo[3.3.1]nona-2,6-diene ligands were synthesized from easily available bicyclo[3.3.1]nonane-2,6-dione and utilized in the asymmetric 1,4-addition reaction of arylboronic acids to cyclic enones. The catalyst prepared in situ from ligand 4b and [RhCl(C2H4)2]2 exhibited excellent catalytic activity and high enantioselectivity (up to 96 % ee) under mild reaction conditions with high atom efficiency.

    2. Corroles

      Control of Oligomerization and Oxidation Steps in the Synthesis of Tris(pentafluorophenyl)corrole (pages 3022–3025)

      Carl Blumenfeld, Katherine J. Fisher, Lawrence M. Henling, Robert H. Grubbs, Harry B. Gray and Scott C. Virgil

      Article first published online: 1 APR 2015 | DOI: 10.1002/ejoc.201500276

      Thumbnail image of graphical abstract

      The mechanistic features of oligomerization and oxidative cyclization steps in the synthesis of tris(pentafluorophenyl)corrole (1) are presented. Analysis of isolated intermediates allowed for the identification of conditions for complete end-capping with pyrrole. Conditions were also optimized for the controlled oxidation to the desired corrole 1. An 84 % yield was achieved during oxidation of the isolated precursor 6 and a 17 % overall yield of 1 was achieved on scale.

    3. Diamine Synthesis

      Direct Catalytic Asymmetric Mannich-Type Reaction of Benzyl Isocyanide: Stereoselective Synthesis of 1,2-Diarylethylenediamines (pages 3026–3031)

      Keiji Tamura, Naoya Kumagai and Masakatsu Shibasaki

      Article first published online: 2 APR 2015 | DOI: 10.1002/ejoc.201500336

      Thumbnail image of graphical abstract

      Enantioenriched 4,5-diarylimidazolines were directly accessed by catalytic asymmetric C–C bond-forming reaction of benzyl isocyanide and N-(thiophosphinoyl)aldimines. The imidazolines were readily transformed into enantioenriched 1,2-diarylethylenediamines.

    4. Cyclotrimerizations

      Rhodium(III)-Catalyzed [2+2+2] Cyclotrimerization of Diynes with Maleic Anhydrides as Alkyne Equivalents (pages 3032–3035)

      Takanori Matsuda and Kentaro Suzuki

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500252

      Thumbnail image of graphical abstract

      Substituted maleic anhydrides act as alkyne equivalents in a rhodium(III)-catalyzed reaction with 1,6-diynes to achieve a formal [2+2+2] cyclotrimerization.

    5. Fluorinated Amino Acids

      Flow Synthesis of Fluorinated α-Amino Acids (pages 3036–3039)

      Stella Vukelić, Dmitry B. Ushakov, Kerry Gilmore, Beate Koksch and Peter H. Seeberger

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500300

      Thumbnail image of graphical abstract

      An efficient, semi-continuous, and protecting-group-free method for the synthesis of fluorinated α-amino acids from the corresponding amines has been developed. A low temperature photooxidative cyanation of benzylic and aliphatic amines provided α-amino nitriles with varying fluorination patterns. These unstable intermediates were trapped with an acid-mediated hydrolysis with good overall yields.

    6. Intramolecular Heck Reaction

      Synthesis of Rigid Analogues of Flavone by Intramolecular Heck Reaction (pages 3040–3043)

      Chuanwei Hou, Hao Chen, Xing Xu, Fangxia Zhu, Lei Guo, Min Jiang, Chunhao Yang and Lianfu Deng

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500180

      Thumbnail image of graphical abstract

      As the title reaction shows, rigid analogues of flavone were synthesized by an intramolecular Heck reaction from 3-(2-bromobenzyl)-4H-chromen-4-ones, which could be prepared easily in two steps. Most compounds were obtained with moderate to good yields.

    7. Iron Catalysis

      Iron-Catalyzed α-Methylenation of Ketones with N,N-Dimethylacetamide: An Approach for α,β-Unsaturated Carbonyl Compounds (pages 3044–3047)

      Yi-Ming Li, Shao-Jie Lou, Qin-Hua Zhou, Lian-Wen Zhu, Long-Feng Zhu and Lei Li

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500189

      Thumbnail image of graphical abstract

      A general and facile iron-catalyzed α-methylenation of carbonyl compounds by using N-methyl amides as the one-carbon source was developed. Various carbonyl compounds (aryl- or alkyl-substituted, enones, 1,3-dicarbonyl compounds) were well tolerated to furnish the corresponding α,β-unsaturated carbonyl compounds in the presence of an iron catalyst, peroxides, and N-methyl amides under aerobic conditions.

    8. Smiles Rearrangement

      One-Pot Synthesis of N-Aryl-Nicotinamides and Diarylamines Based on a Tunable Smiles Rearrangement (pages 3048–3052)

      Shihui Liu, Shaofan Zhu, Ying Wu, Jiayu Gao, Pengfei Qian, Yanwei Hu, Linsen Shi, Shaohua Chen, Shilei Zhang and Yinan Zhang

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500222

      Thumbnail image of graphical abstract

      A substituent-mediated Smiles rearrangement to N-aryl-nicotinamides and diarylamines has been developed. In addition to the wide range of heterocyclic building blocks, the one-pot process also provides an efficient access to an on-market fungicide, boscalid.

    9. Single-Walled Carbon Nanotubes

      Synthesis of Robust Precursors for the Controlled Fabrication of (6,6), (8,8), (10,10), and (12,12) Armchair Single-Walled Carbon Nanotubes (pages 3053–3056)

      Andreas Mueller and Konstantin Yu. Amsharov

      Article first published online: 1 APR 2015 | DOI: 10.1002/ejoc.201500266

      Thumbnail image of graphical abstract

      We report four robust precursors for the rational synthesis of isomerically pure armchair single-walled carbon nanotubes (SWCNTs). The precursor structures are specially “programmed” for fabrication of ultrashort (6,6), (8,8), (10,10), and (12,12) singly capped nanotubes bearing three CNT segments, effective seeds for controlled growth of helicity-pure SWCNTs by metal-catalyzed epitaxial elongation.

  6. Full Papers

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

      Structure and Absolute Configuration of Auriculamide, a Natural Product from the Predatory Bacterium Herpetosiphon aurantiacus (pages 3057–3062)

      Sebastian Schieferdecker, Nicole Domin, Christine Hoffmeier, Donald A. Bryant, Martin Roth and Markus Nett

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500181

      Thumbnail image of graphical abstract

      Chemical analysis of culture extracts from the predatory bacterium Herpetosiphon aurantiacus led to the discovery of the new natural product auriculamide, the structure of which was elucidated by MS and NMR analyses. The absolute configuration was determined, after hydrolysis, by chromatographic comparison with synthetic standards. A gene cluster for the biosynthesis of auriculamide is proposed.

    2. Functionalization of Nanostructures

      Epoxidation of Multi-Walled Carbon Nanotubes by Organocatalytic Oxidation (pages 3063–3068)

      Cosimo Annese, Lucia D'Accolti, Valentina Armuzza, Tatiana Da Ros and Caterina Fusco

      Article first published online: 31 MAR 2015 | DOI: 10.1002/ejoc.201500107

      Thumbnail image of graphical abstract

      An efficient method for the epoxidation of multi-walled carbon nanotubes (MWCNTs) is proposed. It leads to the production of materials that can be easily further functionalized by nucleophiles. Complete chemical (TGA, FTIR, XPS, Raman) and morphological (TEM) characterization of the materials has revealed a high degree of functionalization.

    3. Fluorinated Compounds

      Difluoromethyl and Chlorofluoromethyl Sulfoximines: Synthesis and Evaluation as Electrophilic Perfluoroalkylating Reagents (pages 3069–3075)

      Bruce Pégot, Céline Urban, Aaron Bourne, Thanh Nghi Le, Sébastien Bouvet, Jérôme Marrot, Patrick Diter and Emmanuel Magnier

      Article first published online: 26 MAR 2015 | DOI: 10.1002/ejoc.201500201

      Thumbnail image of graphical abstract

      Bromodifluoromethyl and dichlorofluoromethyl sulfoximines are transformed into the Hu electrophilic difluoromethylating reagent, and into a new chlorofluoromethylating reagent, respectively.

    4. Heterocyclic Spiro Compounds

      Tandem Prins Strategy for the Synthesis of Spiropyrrolidine and Spiropiperidine Derivatives (pages 3076–3085)

      Basi V. Subba Reddy, Suresh Yarlagadda, C. Ravikumar Reddy, M. Rajashekhar Reddy, Balasubramanyan Sridhar, Dayaka Satyanarayana and Bharatam Jagadeesh

      Article first published online: 2 APR 2015 | DOI: 10.1002/ejoc.201500215

      Thumbnail image of graphical abstract

      Cascade reactions between a 3-[(3-methylbut-2-enylamino)methyl]but-3-en-1-ol derivative and aldehydes in the presence of TMSOTf at 0 °C afford the corresponding spiropyrrolidine derivatives in good yields. Similar cyclization of a 3-[(4-methylpent-3-enylamino)methyl]but-3-en-1-ol derivative and aldehydes provides the corresponding spiropiperidines.

    5. Natural Products

      Armochaetoglobins K–R, Anti-HIV Pyrrole-Based Cytochalasans from Chaetomium globosum TW1-1 (pages 3086–3094)

      Chunmei Chen, Hucheng Zhu, Jianping Wang, Jing Yang, Xiao-Nian Li, Jing Wang, Keliang Chen, Yanyan Wang, Zengwei Luo, Guangmin Yao, Yongbo Xue and Yonghui Zhang

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201403678

      Thumbnail image of graphical abstract

      Eight rare pyrrole-based cytochalasans, armochaetoglobins K–R, were isolated from the solid culture broth of the fungus Chaetomium globosum, first isolated from the arthropod Armadillidium vulgare. Among them, armochaetoglobins L–N, Q, and R showed significant anti-HIV activities, with EC50 values ranging from 0.25 to 0.55 µM, and selective index (SI) values ranging from 20.43 to 75.42.

    6. Auxiliary-Mediated Ligation

      A Photocleavable Auxiliary for Extended Native Chemical Ligation (pages 3095–3102)

      Christina Nadler, André Nadler, Christine Hansen and Ulf Diederichsen

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500033

      Thumbnail image of graphical abstract

      A UV-labile auxiliary for cysteine-free peptide ligation reactions was developed. This auxiliary, which is easily prepared, can be readily attached to a variety of N-terminal amino acids to facilitate ligation reactions at various junctions, and its cleavage efficiently proceeds through a mild photolysis reaction. This new auxiliary provides an excellent alternative to existing ligation auxiliaries.

    7. Heterocyclic Chemistry

      Tandem Prins Cyclization for the Stereoselective Synthesis of the 4,5-Diaryl-hexahydropyrano[3,4-c]chromene Skeleton of Calyxins I and J (pages 3103–3108)

      Basi V. Subba Reddy, Mittapalli Ramana Reddy, Sama Gopal Reddy, Balasubramanyan Sridhar and Singarapu Kiran Kumar

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500117

      Thumbnail image of graphical abstract

      A Prins-type bicyclization strategy for the stereoselective synthesis of trans-fused hexahydropyrano[3,4-c]chromene derivatives in good to excellent yields is reported.

    8. Diastereoselective Mannich Reactions

      Synthesis of Chiral β-Aminomalonates from 2-Chlorotetrafluoroethanesulfinyl Aldimines through the Mannich Reaction (pages 3109–3115)

      Kai Yang, Min Jiang and Jin-Tao Liu

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500134

      Thumbnail image of graphical abstract

      An efficient method for the synthesis of chiral β-aminomalonates in good yields and with high diastereoselectivities was achieved through Mannich reactions between 2-chlorotetrafluoroethanesulfinyl aldimines and dialkyl malonates in the presence of N-trimethylsilylimidazole.

    9. Peptide Coupling

      EDC·HCl and Potassium Salts of Oxyma and Oxyma-B as Superior Coupling Cocktails for Peptide Synthesis (pages 3116–3120)

      Yahya E. Jad, Sherine N. Khattab, Beatriz G. de la Torre, Thavendran Govender, Hendrik G. Kruger, Ayman El-Faham and Fernando Albericio

      Article first published online: 31 MAR 2015 | DOI: 10.1002/ejoc.201500142

      Thumbnail image of graphical abstract

      We have shown that combinations of rather simple and green reagents, such as EDC·HCl and the potassium salt of OxymaPure or Oxyma-B, give unique results in terms of yield and low levels of racemization. We envisage a broad application of these reagents in solid-phase and solution synthesis, and especially in the preparation of peptide-based nanomaterials.

    10. Synthetic methods

      Synthesis of Fluorine-Containing 3,3-Disubstituted Oxetanes and Alkylidene Oxetanes (pages 3121–3128)

      Romain Laporte, Anais Prunier, Emmanuel Pfund, Vincent Roy, Luigi A. Agrofoglio and Thierry Lequeux

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500172

      Thumbnail image of graphical abstract

      Access to fluoroalkylidene-oxetanes and -azetidines was realized from four-membered cyclic ketones and fluorosulfones.

    11. Nitrogen Heterocycles

      Synthesis of Diazirine-Based Photoreactive Saccharin Derivatives for the Photoaffinity Labeling of Gustatory Receptors (pages 3129–3134)

      Lei Wang, Takuma Yoshida, Yasuyuki Muto, Yuta Murai, Zetryana Puteri Tachrim, Akiko Ishida, Shiori Nakagawa, Yasuko Sakihama, Yasuyuki Hashidoko, Katsuyoshi Masuda, Yasumaru Hatanaka and Makoto Hashimoto

      Article first published online: 1 APR 2015 | DOI: 10.1002/ejoc.201500184

      Thumbnail image of graphical abstract

      Saccharin is one of the most common artificial sweeteners. Synthesis of photoreactive saccharin derivatives that contain a (trifluoromethyl)diazirinyl moiety at the 5- or 6-position is reported. These saccharin derivatives could be applied for functional analysis of gustatory receptors.

    12. α-Acyloxylation Reaction

      nBu4NI-Catalyzed α-Benzoxylation of Ketones with Terminal Aryl Alkenes (pages 3135–3140)

      Buddhadeb Mondal, Subas Chandra Sahoo and Subhas Chandra Pan

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500233

      Thumbnail image of graphical abstract

      An efficient synthesis for the α-benzoxylation of aryl ketones has been developed by using terminal aryl alkenes as the arylcarboxy surrogate. The products were obtained in moderate to good yields for a broad scope of substrates. Tetra-n-butylammonium iodide (TBAI) and tert-butyl hydroperoxide (TBHP) were employed as the catalyst and oxidant, respectively.

    13. Organocatalysis

      Copper(I)-Catalysed Domino Coupling and Cyclisation Reaction: A Mild, Expedient Route for the Synthesis of Indene and Dihydronaphthalene Derivatives (pages 3141–3146)

      Gullapalli Kumaraswamy and Guniganti Balakishan

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500284

      Thumbnail image of graphical abstract

      Bench-top CuI has been used as a catalyst to obtain a series of functionalised indene, dihydronaphthalene and cyclohexenone derivatives. Notably, the substrates were combined at a 1:1 ratio and no trace of fumarate or maleate side products were observed in spite of using diazo substrate and copper catalyst.

    14. Propargylic Substitution

      Palladium-Catalyzed Nucleophilic Substitution of Propargylic Carbonates and Meldrum's Acid Derivatives (pages 3147–3151)

      Ilaria Ambrogio, Sandro Cacchi, Giancarlo Fabrizi, Antonella Goggiamani and Antonia Iazzetti

      Article first published online: 2 APR 2015 | DOI: 10.1002/ejoc.201500337

      Thumbnail image of graphical abstract

      Propargylic carbonates react with Meldrum's acid derivatives in the presence of Pd(OAc)2 and P(2-furyl)3 in THF at 80 °C to give propargylic substitution products.

    15. Total Synthesis

      Total Synthesis of the Putative Structure of Deoxypumiliotoxin 193H by an Ireland–Claisen Rearrangement (pages 3152–3156)

      Gints Smits and Ronalds Zemribo

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500063

      Thumbnail image of graphical abstract

      A stereoselective total synthesis of 8-deoxypumiliotoxin 193H is described. The concise total synthesis features the use of readily available starting materials, namely, natural amino acids and the Ireland–Claisen rearrangement as the key stereochemistry controlling step.

    16. Expanded Porphyrins

      Multi-Expanded Porphyrin Assemblies on Cyclophosphazene Scaffolds (pages 3157–3163)

      Tejinder Kaur, Tamanna K. Khan and Mangalampalli Ravikanth

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500131

      Thumbnail image of graphical abstract

      Hexasapphyrin and octasapphyrin assemblies on cyclophosphazene scaffolds were synthesized in decent yields, and their molecular structures were elucidated by 1D and 2D NMR spectroscopy.

    17. Cascade Synthesis of Pyrroles

      Synthesis of Polysubstituted Pyrroles from Activated Alkynes and N-Propargylamines through Base-Catalyzed Cascade Reaction (pages 3164–3170)

      Jianquan Weng, Yong Chen, Binjie Yue, Meng Xu and Hongwei Jin

      Article first published online: 26 MAR 2015 | DOI: 10.1002/ejoc.201500166

      Thumbnail image of graphical abstract

      An efficient method for the synthesis of polysubstituted pyrroles from activated alkynes and N-propargylamines has been developed. This cascade process represents an atom- and step-economical way to construct a range of polysubstituted pyrroles and involves base-catalyzed Michael addition/alkyne carbocyclization or Michael addition/aza-Claisen rearrangement/cyclization.

    18. β-Oxo Amides

      Silver(I)-Catalyzed Tandem Approach to β-Oxo Amides (pages 3171–3177)

      Jaya Kishore Vandavasi, Cheng-Tien Hsiao, Wan-Ping Hu, Siva Senthil Kumar Boominathan and Jeh-Jeng Wang

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500224

      Thumbnail image of graphical abstract

      A new, catalytic approach to the synthesis of β-oxo amides from β-oxo esters with a broad substrate scope in good to excellent yields was developed. In situ NMR spectroscopy and crossover experiments confirmed the reaction mechanism.

SEARCH

SEARCH BY CITATION