European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 15

May 2015

Volume 2015, Issue 15

Pages 3183–3384

  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
      Connecting Electron-Deficient and Electron-Rich Aromatics to Support Intermolecular Interactions in Crystals (Eur. J. Org. Chem. 15/2015)

      Markus Albrecht, Hai Yi, Fangfang Pan, Arto Valkonen and Kari Rissanen

      Article first published online: 12 MAY 2015 | DOI: 10.1002/ejoc.201590039

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      The cover picture shows, in the background, the contact area and charge distribution of the π-complex between electron-rich benzene and electron-deficient hexafluorobenzene. Besides hydrogen bonding (including CF···H interactions), this interaction represents a major structure-controlling force in the crystal formation of compounds containing electron-deficient pentafluorophenyl as well as more electron-rich aromatic groups as substituents. Two examples of this interaction in crystal structures are shown in the foreground of the picture. Details are discussed in the article by M. Albrecht, K. Rissanen et al. on 3235 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
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    1. Natural Product Synthesis

      Progress in the Preparation of Jatrophane Diterpenes (pages 3197–3219)

      Uwe Rinner

      Article first published online: 19 MAR 2015 | DOI: 10.1002/ejoc.201403598

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      Jatrophane diterpenes are fascinating natural products, obtained from species of the Euphorbiaceae plant family. The biosynthesis of Euphorbiaceae constituents as well as their biological properties are briefly outlined followed by a detailed discussion of syntheses and approaches to jatrophane diterpenes.

  5. Short Communications

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

      Preparation and Crystal Structure of the 1,3-alternate Atropisomer of a Calix[4]radialene (pages 3221–3225)

      Norbert Itzhak and Silvio E. Biali

      Article first published online: 20 APR 2015 | DOI: 10.1002/ejoc.201500319

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      A rigid calix[4]radialene was prepared and structurally characterized. The crystal structure determination corroborates the presence of the four exocyclic double bonds and the 1,3-alternate arrangement of the aryl rings.

    2. Direct C–H Arylations

      Palladium-Catalyzed Direct C–H Arylation of Dicyanobenzenes (pages 3226–3229)

      Netta E. Ihanainen, Esa T. T. Kumpulainen and Ari M. P. Koskinen

      Article first published online: 20 APR 2015 | DOI: 10.1002/ejoc.201500288

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      A direct palladium-catalyzed C–H arylation method to synthesize biaryls from dicyanobenzenes and other electron-deficient benzonitriles has been developed. A variety of functional groups are tolerated, and yields up to 83 % can be obtained.

    3. 1,3-Selenazoles

      One-Pot Synthesis of 2-Amino-1,3-selenazole via an Intermediary Amidinoselenourea (pages 3230–3234)

      Alok Ranjan, Ragini Yerande, Mahantesh Jadhav, Swapnil G. Yerande and Dattatraya H. Dethe

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500168

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      An efficient method for the synthesis of 2-amino-1,3-selenazole by a sequential one-pot multicomponent reaction between isoselenocyanate and N,N-diethyl-amidine has been developed. It represents a step-economical way to construct a range of 2-amino-1,3-selenazole derivatives in 65–89 % yields. The structure of the trisubstituted selenazole formed was unambiguously established by X-ray crystallography.

  6. Full Papers

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

      Connecting Electron-Deficient and Electron-Rich Aromatics to Support Intermolecular Interactions in Crystals (pages 3235–3239)

      Markus Albrecht, Hai Yi, Fangfang Pan, Arto Valkonen and Kari Rissanen

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500175

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      Polar effects introduced by a combination of electron-poor and electron-rich aromatics within one compound control the packing of the crystal based on intermolecular hydrogen bonding, aryl···aryl interactions, and even uncommon non-classical CF···HC hydrogen bonding.

    2. Total Synthesis

      Total Synthesis of (±)-8-Oxo-erythrinine, (±)-8-Oxo-erythraline, and (±)-Clivonine (pages 3240–3250)

      Maomao He, Chunrong Qu, Bingbing Ding, Hao Chen, Yangyan Li, Guofu Qiu, Xianming Hu and Xuechuan Hong

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500265

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      Total syntheses of the erythrina alkaloids (±)-8-oxo-erythrinine and (±)-8-oxo-erythraline have been developed, based on an intramolecular 6-exo-trig radical cyclization of a highly functionalized enamide (X = O, n = 1). An improved linear total synthesis of the amaryllidaceae alkaloid (±)-clivonine through a 6-endo-trig cyclization of a similar intermediate (X = O, n = 0) is also reported.

    3. Gold(I) Catalysis

      Gold-Catalysed Synthesis of Exocyclic Vinylogous Amides and β-Amino Ketones: A Detailed Study on the 5-exo/6-endo-dig Selectivity, Methodology and Scope (pages 3251–3265)

      Dina Scarpi, Stefano Begliomini, Cristina Prandi, Alberto Oppedisano, Annamaria Deagostino, Enrique Gómez-Bengoa, Béla Fiser and Ernesto G. Occhiato

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500205

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      The gold(I)-catalysed reaction of N-alkoxycarbonyl-protected 6-alkynyl-3,4-dihydro-2H-pyridines gives synthetically useful vinylogous amides (β-enaminones). The 6-endo-dig approach is exclusive with substituted alkynes, whereas with terminal alkynes the 5-exo-dig cyclization prevails. The extension of the approach to β-amino ketones is also described.

    4. Natural Products

      Collective Synthesis of Natural Products Sharing the Dihydro-γ-Ionone Core (pages 3266–3273)

      Alexis Castillo, Lucia Silva, David Briones, José F. Quílez del Moral and Alejandro F. Barrero

      Article first published online: 16 APR 2015 | DOI: 10.1002/ejoc.201500208

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      The expedient enantioselective synthesis of several natural products from a common precursor, (+)-3,4-dihydro-γ-ionone, is described. The production of this natural compound in multigram scale from the extract Bellardia trixago is the basis of this approach.

    5. Salicyldialdehyde Synthesis

      Synthesis of para-Aryl-Substituted Salicyldialdehydes (pages 3274–3285)

      Dennis Reinhard, Ludger Schöttner, Victor Brosius, Frank Rominger and Michael Mastalerz

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500228

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      Two complementary synthetic routes to 4-arylsalicyldialdehydes are elaborated and compared for various substrates. Unexpected byproducts as well as preliminary results on cage formation are also discussed.

    6. Catalytic Olefinations

      Phospholane-Catalyzed Wittig Reaction (pages 3286–3295)

      Thomas Werner, Marcel Hoffmann and Sunetra Deshmukh

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500243

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      A suitable and potentially tunable catalyst for the catalytic Wittig reaction is presented. The scope and limitations of this catalyst were evaluated, and over 20 examples are reported. Moreover, efforts to utilize chiral analogues of the catalyst for the desymmetrization of a pro-chiral diketone are reported.

    7. Synthetic Methods

      Regioisomerically Pure 1,7-Dibromo-Substituted Perylene Bisimide Dyes: Efficient Synthesis, Separation, and Characterization (pages 3296–3302)

      Jiajun Ma, Leicheng Yin, Gang Zou and Qijin Zhang

      Article first published online: 9 APR 2015 | DOI: 10.1002/ejoc.201500206

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      1,7-Dibromo-substituted perylene bisimides have been isolated from regioisomeric mixtures by column chromatography in yields of at least 60 %. The 1,7-disubstituted intermediates can provide a convenient and efficient approach to novel perylene bisimide derivatives.

    8. Pd-Catalyzed α-Arylation

      Umpolung Pd-Catalyzed α-Arylation Reactions in Natural Product Synthesis: Syntheses of (+)-Xestodecalactone A, (–)-Curvularin, (+)-12-Oxocurvularin and (–)-Citreofuran (pages 3303–3313)

      Dripta De Joarder and Michael P. Jennings

      Article first published online: 14 APR 2015 | DOI: 10.1002/ejoc.201500287

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      The total syntheses of (+)-xestodecalactone A, (–)-curvularin, and formal syntheses of (+)-12-oxocurvularin and (–)-citreofuran have been accomplished by utilizing a unified strategy of an umpolung Pd-catalyzed α-arylation of complex α-bromo esters and boronic acids under mild reaction conditions.

    9. Organic Synthesis

      Synthesis of Enantiopure 1,5-Enynes and 1,5-Diynes with Propargylic Quaternary Centers (pages 3314–3319)

      Ignacio Pérez, Francisco Yuste, Rubén Sánchez-Obregón, Rubén A. Toscano, José Alemán, Leyre Marzo, Ana M. Martín Castro, Inés Alonso and José Luis García Ruano

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500004

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      Diastereoselective quaternization of o-sulfinylbenzyl-methylpropargylic carbanions has been achieved with allylic, propargylic, and benzylic halides. The stereoselectivity is efficiently controlled by the sulfinyl group, acting as a remote chiral auxiliary. This method provides access to enantiopure 1,5-enynes, 1,5-diynes, and 4-arylalkynes bearing quaternary propargylic centers.

    10. Organocatalysis

      Highly Enantioselective Synthesis of Chiral Pyranonaphthoquinone-Fused Spirooxindoles through Organocatalytic Three-Component Cascade Reactions (pages 3320–3326)

      Hong-Wu Zhao, Bo Li, Ting Tian, Wei Meng, Zhao Yang, Xiu-Qing Song, Xiao-Qin Chen and Hai-Liang Pang

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500152

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      In the presence of cinchona-thiourea catalyst C1, the developed organocascade three-component reaction of isatins, malononitrile, and 2-hydroxynaphthalene-1,4-diones readily proceeded to furnish desired chiral pyranonaphthoquinone-fused spirooxindoles in excellent chemical yields and high enantioselectivities (up to 99 % yield and 97 % ee).

    11. Tandem Reactions

      Synthesis of Multisubstituted Dihydroquinoxaline Derivatives by Tandem N-Alkylation and Addition Reactions of 3-Oxoquinoxaline-2-carboxylates (pages 3327–3337)

      Satoru Miyamaru, Kazuto Umezu, Akinori Ito and Makoto Shimizu

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500225

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      A one-pot synthesis of multisubstituted dihydroquinoxalin-2-ones using umpolung N-alkylation followed by oxidation and C-alkylation reaction is described. The synthesis of tricyclic compounds containing a dihydroquinoxaline skeleton was then carried out by ring closing metathesis (RCM) of N,C-bis-addition products containing olefins.

    12. Sulfoximines

      The Synthesis of Chiral Benzothiazine and Thiazinoquinoline Derivatives (pages 3338–3343)

      Long Wang, Daniel L. Priebbenow, Xiao Yun Chen, Fang-Fang Pan and Carsten Bolm

      Article first published online: 10 APR 2015 | DOI: 10.1002/ejoc.201500250

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      2,1-Benzothiazine and thiazinoquinoline derivatives were prepared by using an 8-amino-2,1-benzothiazine as a key intermediate. These compounds are rigid variants of a highly enantioselective sulfoximine ligand that was previously used for copper-catalyzed Mukaiyama-type aldol reactions. Our derivatives actively catalyzed the same C–C bond formation but with much lower enantioselectivities.

    13. Transfer Hydrogenation

      Highly Enantioselective SPINOL-Derived Phosphoric Acid Catalyzed Transfer Hydrogenation of Diverse C=N-Containing Heterocycles (pages 3344–3351)

      Yiliang Zhang, Rong Zhao, Robert Li-Yuan Bao and Lei Shi

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500330

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      Chiral SPINOL-derived phosphoric acids are highly enantioselective catalysts for the asymmetric transfer hydrogenation of diversely substituted C=N-containing heterocyclic compounds (SPA = SPINOL-derived phosphoric acids). The method provides straightforward access to various optically active tetrahydroquinolines and dihydro-2H-1,4-benzothiazines in high yields with excellent enantioselectivities.

    14. Conjugate Addition

      Synthesis of Boron- and Silicon-Containing Amino Acids through Copper-Catalysed Conjugate Additions to Dehydroalanine Derivatives (pages 3352–3360)

      Francesca Bartoccini, Silvia Bartolucci, Simone Lucarini and Giovanni Piersanti

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500362

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      Copper mediated β-boration and β-silylation of a variety of dehydroalanine and dehydropeptide compounds gives ready access to orthogonally N- and C-protected boron- and silicon-containing amino acids and small peptides.

    15. Modular Cyclization

      Tandem Arylation/Friedel–Crafts Reactions of o-Acylanilines with Diaryliodonium Salts: A Modular Synthesis of Acridine Derivatives (pages 3361–3369)

      Xinlong Pang, Zhenbang Lou, Ming Li, Lirong Wen and Chao Chen

      Article first published online: 9 APR 2015 | DOI: 10.1002/ejoc.201500161

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      A tandem cyclization reaction to produce acridine derivatives was realized with o-acylanilines and diaryliodonium salts under Cu-catalyzed or metal-free reaction conditions at elevated temperature.

    16. H–D Exchange

      A Simple and Cost-Effective Method for the Regioselective Deuteration of Phenols (pages 3370–3373)

      Miao Zhan, Ruixue Xu, Ye Tian, Hongxia Jiang, Lifeng Zhao, Yongmei Xie and Yuanwei Chen

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500192

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      An efficient method for the synthesis of regioselectively deuterated phenols under microwave irradiation was developed. The method also allowed the deuteration of complex pharmaceutically interesting substrates.

    17. Regioselective Coupling

      Synthesis of Diiodinated Biphenyls and Iodinated meta-Terphenyls by Regioselective Suzuki–Miyaura Cross-Coupling Reactions of 5-Substituted 1,2,3-Triiodobenzenes (pages 3374–3384)

      Raed M. Al-Zoubi, Walid K. Al-Jammal, Mohammad Y. El-Khateeb and Robert McDonald

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500263

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      A facile and efficient one-step method is reported for the synthesis of 2,3-diiodinated biphenyl and iodinated meta-terphenyl derivatives by employing Suzuki–Miyaura cross-coupling reactions of 5-substituted 1,2,3-triiodobenzenes. This reaction is general in scope, scalable, and highly regioselective.

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