Asian Journal of Organic Chemistry

Cover image for Vol. 4 Issue 6

Early View (Online Version of Record published before inclusion in an issue)

Editor: Richard Threlfall; Editorial Board Chairs: Sung Ho Kang, Keiji Maruoka, Deqing Zhang

Impact Factor: 2.292

ISI Journal Citation Reports © Ranking: 2013: 27/58 (Chemistry Organic)

Online ISSN: 2193-5815

Associated Title(s): Advanced Synthesis & Catalysis, Chemistry – An Asian Journal, ChemNanoMat, European Journal of Organic Chemistry

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  1. 1 - 16
  1. Full Papers

    1. Molecular Orbitals

      Geometrical Dependence of the Highest Occupied Molecular Orbital in Bicyclic Systems: π-Facial Stereoselectivity of Bicyclic and Tricyclic Olefins

      Motonori Tsuji

      Article first published online: 29 MAY 2015 | DOI: 10.1002/ajoc.201500054

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      Choosing sides: An interpretation of the stereochemical preference of electrophilic attacks of olefins in bicyclic and tricyclic systems is proposed. The selectivity of these systems is thought to be controlled by two types of HOMO, which are formed by a combination of different orbitals, depending on the geometrical conditions.

    2. Glycosylation

      Effective Synthesis of α-d-GlcN-(1[RIGHTWARDS ARROW]4)-d-GlcA/l-IdoA Glycosidic Linkage under Gold(I) Catalysis

      Dr. Jiakun Li, Yuanwei Dai, Dr. Wei Li, Dr. Stéphane Laval, Dr. Peng Xu and Prof. Dr. Biao Yu

      Article first published online: 29 MAY 2015 | DOI: 10.1002/ajoc.201500113

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      Gold rush: Direct glycosylations between 2-deoxy-2-azido-d-glucopyranosyl (d-GlcN) ortho-hexynylbenzoate donors and uronate acceptors (d-GlcA/l-IdoA) under gold(I) catalysis were performed in high yields with α selectivity, thus constituting an alternative method to construct the difficult α-d-GlcN-(1[RIGHTWARDS ARROW]4)-d-GlcA/l-IdoA glycosidic linkage occurring in heparin and heparan sulfate. PG=protecting group.

    3. Polyaromatic Hydrocarbons

      Facile Synthesis and Phase Behaviors of Monofunctionalized Hexa-peri-hexabenzocoronenes

      Yu Zhou, Meng-Yao Zhang, Ke-Hua Gu, Yu-Feng Zhu, Xing-He Fan and Zhihao Shen

      Article first published online: 29 MAY 2015 | DOI: 10.1002/ajoc.201500131

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      The one and only: A method for synthesizing monofunctionalized hexa-peri-hexabenzocoronenes was developed by loading dialkyl-diphenylacetylenes and asymmetric diphenylacetylene derivatives at the same time catalyzed by [Co2(CO)8].

  2. Communications

    1. Hydroboration

      Copper-Catalyzed β-Selective Hydroborylation of Ynamides: A Facile Access to (E)-β-Alkenylamide Boronates

      Prof. Dr. Yihui Bai, Fang Zhang, Jiajia Shen, Fang Luo and Prof. Dr. Gangguo Zhu

      Article first published online: 29 MAY 2015 | DOI: 10.1002/ajoc.201500119

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      On the beta: A Cu-catalyzed, highly β-selective hydroboration of ynamides with bis(pinacolato)diboron as the hydroboration reagent is reported, providing a good complementary regioselectivity to the existing methods.

  3. Full Papers

    1. Organic Electronics

      An Electron-Accepting Chromophore Based on Fluorene and Naphthalenediimide Building Blocks for Solution-Processable Bulk Heterojunction Devices

      Dr. Akhil Gupta, Xizu Wang, Doli Srivani, Dr. Ben Alford, Dr. Vijila Chellappan, Dr. Ante Bilic, Hemlata Patil, Dr. Lathe A. Jones, Dr. Sidhanath V. Bhosale, Dr. Prashant Sonar and Dr. Sheshanath V. Bhosale

      Article first published online: 18 MAY 2015 | DOI: 10.1002/ajoc.201500112

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      No balls, please: A unique, non-fullerene, electron-accepting chromophore (B2) was designed, synthesized, and successfully used in solution-processable bulk heterojunction devices. A power conversion efficiency of 1.16 % was achieved for primitive bulk heterojunction devices with a high fill factor of approximately 54 %. This fill factor is among the highest reported for non-fullerene acceptors.

  4. Communications

    1. Heck Reaction

      Manganese-Catalyzed Alkyl-Heck-Type Reaction via Oxidative Decarbonylation of Aldehydes

      Zhenzhen Zong, Wenxiao Wang, Xiaohui Bai, Hui Xi and Prof. Dr. Zhiping Li

      Article first published online: 14 MAY 2015 | DOI: 10.1002/ajoc.201500148

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      Man power: An alkyl-Heck-type cross-coupling reaction is developed by manganese-catalyzed oxidative decarbonylation of aldehydes. A variety of primary, secondary, and tertiary aliphatic aldehydes can participate in this alkenylation. The reaction is initiated by an alkyl radical, which is generated by oxidative decarbonylation of the aldehyde.

    2. Organocatalysis

      Organocatalytic Asymmetric Vinylogous Michael Addition of 3-(2-Oxoindolin-3-ylidene)butanoates to Nitroalkenes Catalyzed by a Bifunctional Cinchona-Based Squaramide

      Chen Zheng, Hai-Feng Wang, Wei-Qi Chen, Wen-Xue Chen and Fen-Er Chen

      Article first published online: 7 MAY 2015 | DOI: 10.1002/ajoc.201500111

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      Stereo Mike: A highly enantioselective vinylogous Michael addition of 3-(2-oxoindolin-3-ylidene)butanoates to nitroalkenes catalyzed by a cinchona-based squaramide bifunctional organocatalyst is disclosed. This method provides a series of chiral products with excellent enantioselectivity of up to 99 % ee and diastereoselectivity of greater than 20:1.

  5. Full Papers

    1. Total Synthesis

      Synthesis of (−)-Deoxynupharidine by Allenic Hydroxylamine Cyclisation

      Prof. Roderick W. Bates, Dr. Chia Juan Lim, Dr. Steven J. Collier and Dr. Joly Sukumaran

      Article first published online: 7 MAY 2015 | DOI: 10.1002/ajoc.201500094

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      What’s Nu? (−)-Deoxynupharidine has been synthesised via an intermediate that can also be used for other Nuphar alkaloids. A highly diastereoselective silver catalysed cyclisation of an allenic hydroxylamine sets the stereochemistry in this synthesis.

    2. Organic Electronics

      Synthesis, Characterization, and Memory Performance of Two Phenazine/Triphenylamine-Based Organic Small Molecules through Donor-Acceptor Design

      Chengyuan Wang, Masataka Yamashita, Dr. Benlin Hu, Dr. Yi Zhou, Jiangxin Wang, Dr. Jin Wu, Prof. Dr. Fengwei Huo, Prof. Dr. Pooi See Lee, Prof. Dr. Naoki Aratani, Prof. Dr. Hiroko Yamada and Prof. Dr. Qichun Zhang

      Article first published online: 5 MAY 2015 | DOI: 10.1002/ajoc.201500087

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      Test your memory: Two organic small molecules TPA-2BIPs and TPA-3BIPs have been synthesized and characterized. Sandwich-structure memory devices made from these molecules show that the two materials have similar switching behavior but different ON/OFF ratios. AFM images analysis and molecular simulation indicate that increasing the numbers of acceptors change the stacking of molecules in the solid state, but have less effect on switching behaviors of as-prepared memory devices.

    3. Pentaphyrins

      Synthesis, Structure, and Properties of Core-modified Pentaphyrins Containing Six meso Carbons

      Emandi Ganapathi, Tamal Chatterjee, Way-Zen Lee and Mangalampalli Ravikanth

      Article first published online: 5 MAY 2015 | DOI: 10.1002/ajoc.201500072

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      Six appeal: Pentaphyrins containing six meso carbons were prepared by condensation of butane-2,3-diyl-bisthiophene-2,5-diyl-bis(p-methoxyphenylmethanol) with different meso-aryl tripyrromethanes under mild, acid-catalyzed conditions. The crystal structure shows that the thiophene ring, which is positioned opposite to the ethene bridged meso carbons, is inverted.

  6. Focus Reviews

    1. Sulfur Dioxide Surrogates

      The Development and Application of Sulfur Dioxide Surrogates in Synthetic Organic Chemistry

      Dr. Edward J. Emmett and Prof. Michael C. Willis

      Article first published online: 1 MAY 2015 | DOI: 10.1002/ajoc.201500103

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      Stunt double: The development of non-gaseous sulfur dioxide surrogates has stimulated recent interest in sulfur dioxide chemistry. The result has been the invention of new reactions and catalytic processes leading to valuable sulfonyl-containing molecules. The surrogates, the reactions and applications are all considered in this Focus Review.

  7. Communications

    1. Michael addition

      Chiral Lithium Binaphtholate for Enantioselective Michael Addition of Acyclic α-Alkyl-β-Keto Esters to Vinyl Ketones

      Prof. Dr. Shunsuke Kotani, Miyuki Moritani and Prof. Dr. Makoto Nakajima

      Article first published online: 1 MAY 2015 | DOI: 10.1002/ajoc.201500122

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      A chiral lithium binaphtholate base catalyzes a Michael addition of acyclic α-alkyl-β-keto esters to vinyl ketones in a highly enantioselective manner. The present method is convenient and efficient for the construction of chiral quaternary carbon centers.

    2. Photoaffinity Probes

      Comparative Analysis of the Reactivity of Diazirine-Based Photoaffinity Probes toward a Carbohydrate-Binding Protein

      Prof. Kaori Sakurai, Tomoki Yasui and Sakae Mizuno

      Article first published online: 1 MAY 2015 | DOI: 10.1002/ajoc.201500116

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      Sticking to sugars: A set of lactose-based photoaffinity probes bearing alkyl diazirine and trifluoromethylphenyl diazirine (TPD) groups were designed and synthesized to directly compare their efficiency in photocrosslinking a low-affinity, carbohydrate-binding protein. While the crosslinking efficiency of TPD probes was higher toward a single binding protein, the alkyl diazirine probe proved more selective in photoaffinity labeling studies in cell lysate.

  8. Full Papers

    1. Domino Reactions

      A Catalyst-Free Approach to Construct 3-(Cyclopentenone)oxindoles Through a Phosphine-Ylide-Initiated Triple Domino Sequence

      Yanlong Du, Yufen Liu, Dr. Aimin Yu, Prof. Dabin Qin, Kui Zhang and Prof. Xiangtai Meng

      Article first published online: 29 APR 2015 | DOI: 10.1002/ajoc.201500027

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      Phosphine-Ylide-Initiated Triple Domino Reaction: A phosphine-ylide-initiated triple domino reaction has been developed. Readily available isatin derivatives and phosphine ylide 2 are converted into 3-(cyclopentenone)oxindoles in one step under catalyst-free conditions.

  9. Communications

    1. Aryne Chemistry

      Aryne Reaction with γ-Arylallenylcarboxyamides: Unexpected Diels–Alder Cycloaddition

      Haixing Fu, Yupo Yang, Zhibin Wei, Zhengjuan Zhang, Prof. Dr. Chunrui Wu and Prof. Dr. Feng Shi

      Article first published online: 27 APR 2015 | DOI: 10.1002/ajoc.201500098

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      Aryne antics: Arynes react with γ-arylallenylcarboxyamides in an unexpected Diels–Alder cycloaddition fashion, leading to phenanthrene derivatives. This reaction is drastically different from the analogous aryne reaction with γ-arylallenylcarboxylic acids, where aryne C[BOND]O single bond insertion takes place to afford chromones. This contrast is another example in aryne chemistry where isoelectronic atom replacement leads to completely different reactivity.

  10. Full Papers

    1. Aryltrifluoromethylation

      Metal-Free Direct Aryltrifluoromethylation of Allylic Alcohols with Langlois’ Reagent through Concomitant 1,2-Aryl Migration

      Hong-Li Huang, Hang Yan, Guo-Lin Gao, Chao Yang and Wujiong Xia

      Article first published online: 27 APR 2015 | DOI: 10.1002/ajoc.201500096

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      A highly efficient metal-free strategy to synthesize α-aryl-β-trifluoromethyl ketones through unique 1,2-aryl migration from allylic alcohols has been developed under mild conditions, in which Langloi’s reagent (CF3SO2Na) was used as a cheap CF3 source.

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