Asian Journal of Organic Chemistry

Cover image for Vol. 3 Issue 1

January 2014

Volume 3, Issue 1

Pages 1–81

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Correction
    6. News
    7. Focus Review
    8. Communications
    9. Full Papers
    1. You have free access to this content
      Cover Picture: Palladium-Catalyzed Odorless One-Pot Synthesis of Vinyl Sulfides from Organohalides, Thiourea, and Alkynes (Asian J. Org. Chem. 1/2014) (page 1)

      Jie Feng, Guoping Lu, Meifang Lv and Dr. Chun Cai

      Version of Record online: 17 JAN 2014 | DOI: 10.1002/ajoc.201490000

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      Vinyl sulfides are a class of important synthetic intermediates in organic synthesis. As illustrated on the front cover, the preparation of vinyl sulfides by a three-component reaction of halides, thiourea, and alkynes is reported by Chun Cai and co-workers in their Full Paper on page 77 ff. Two carbon-sulfur bonds are formed in one pot by this palladium [Pd(dppf)Cl2]-catalyzed system. The protocol is free of foul-smelling thiols and is operated under mild conditions to obtain cis-configured anti-Markovnikov products with moderate to excellent yields and excellent selectivity.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Correction
    6. News
    7. Focus Review
    8. Communications
    9. Full Papers
    1. You have free access to this content
      There’s an App for That (pages 3–4)

      Dr. Richard Threlfall

      Version of Record online: 13 JAN 2014 | DOI: 10.1002/ajoc.201300257

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Correction
    6. News
    7. Focus Review
    8. Communications
    9. Full Papers
  4. Correction

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Correction
    6. News
    7. Focus Review
    8. Communications
    9. Full Papers
    1. You have free access to this content
      Correction: An Enantiodivergent Synthesis of (+)- and (−)-Centrolobines by Asymmetric Esterification Catalyzed by (R)-(+)-N-Methylbenzoguanidine ((R)-NMBG) (page 9)

      Dr. Kenya Nakata, Tatsuya Tokumaru, Prof. Dr. Hidetoshi Iwamoto, Prof. Dr. Yutaka Nishigaichi and Prof. Dr. Isamu Shiina

      Version of Record online: 17 JAN 2014 | DOI: 10.1002/ajoc.201300258

  5. News

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Correction
    6. News
    7. Focus Review
    8. Communications
    9. Full Papers
  6. Focus Review

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Correction
    6. News
    7. Focus Review
    8. Communications
    9. Full Papers
    1. Artificial Proteases

      Progress in Designing Artificial Proteases: A New Therapeutic Option for Amyloid Diseases (pages 18–32)

      Prof. Dr. Junghun Suh

      Version of Record online: 11 OCT 2013 | DOI: 10.1002/ajoc.201300135

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      Man-made: This Focus Review describes the evolution of artificial proteases. The evolution took place though discovery of catalytic centers for peptide hydrolysis, attachment of substrate-recognition sites to the catalytic centers, and the advent of target-selective artificial proteases. Application of the target-selective artificial proteases led to a therapeutic option for amyloid diseases, such as Alzheimer's disease and diabetes.

  7. Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Correction
    6. News
    7. Focus Review
    8. Communications
    9. Full Papers
    1. Mukaiyama Aldol Reaction

      Possible Intervention of Prototropic and Silatropic Ene-type Mechanisms in Asymmetric Catalytic Mukaiyama Aldol Reactions (pages 34–40)

      Kazuya Honda and Prof. Dr. Koichi Mikami

      Version of Record online: 27 DEC 2013 | DOI: 10.1002/ajoc.201300226

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      ESE does it: Computational analyses on the ene-type mechanisms in the Mukaiyama aldol reaction between glyoxylate and acetone enol silyl ether (ESE) with allylic hydrogen atoms catalyzed by BINOL-TiIV, bisoxazoline (box)-CuII, and BINAP-PdII complexes were performed. The prototropic and silatropic ene-type mechanisms intervene in these reactions with the ESE C[DOUBLE BOND]C and aldehyde C[DOUBLE BOND]O bonds in close (syn-clinal) proximity for proto- and silatropic ene pathways.

    2. [2+2] Cycloadditions

      A 2-Benzothiazolylphenyl Group Accelerates the Intramolecular [2+2] Cycloaddition of Allene-Ynes (pages 41–43)

      Hiroto Hori, Shigeru Arai and Atsushi Nishida

      Version of Record online: 27 NOV 2013 | DOI: 10.1002/ajoc.201300218

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      A [2+2] cycloaddition reaction of allene-ynes under thermal conditions with/without a metal complex is described. A key feature of this reaction is that a 2-benzothiazolylphenyl group bearing a C[BOND]C triple bonds remarkably promotes the reaction to give the corresponding cyclobutenes with or without metal catalysts.

    3. C[BOND]H Activation

      Metal- and Oxidant-Free Direct sp3 C[BOND]H Arylation of Pyrrolidine (pages 44–47)

      Surajit Haldar, Sujit Mahato and Dr. Chandan K. Jana

      Version of Record online: 28 NOV 2013 | DOI: 10.1002/ajoc.201300233

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      Out of metal! A metal- and oxidant-free method for direct sp3 C[BOND]H arylation of pyrrolidine has been developed. As an alternative to metal-mediated reactions, the method relies on a highly atom economic three-component reaction, which is selective for single regioisomers of aryl pyrrolidines that are important in chemistry as well as in biology. The method, operating under simple and mild reaction conditions, is very efficient, even on a multigram scale.

    4. Ruthenium(II)-Catalyzed Chelation-Assisted Arylation of C[BOND]H Bonds with Diaryliodonium Salts (pages 48–51)

      Jordan Sun Ho, Dr. Luis C. Misal Castro, Yoshinori Aihara, Dr. Mamoru Tobisu and Prof. Dr. Naoto Chatani

      Version of Record online: 19 NOV 2013 | DOI: 10.1002/ajoc.201300199

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      Chelation-assisted arylation of the ortho C[BOND]H bonds in 2-arylpyridine derivatives was achieved by using [Ru(OAc)2(p-cymene)] as the catalyst and diaryliodonium salts as the arylation reagent.

    5. Total Synthesis

      A Concise Stereocontrolled Total Synthesis of (±)-Stemoamide (pages 52–54)

      Zhengnian Li, Prof. Lijuan Zhang and Prof. Dr. Fayang G. Qiu

      Version of Record online: 28 NOV 2013 | DOI: 10.1002/ajoc.201300205

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      Hit for six: (±)-Stemoamide was synthesized in six steps starting from readily accessible 2-trimethylsilioxy-3-methylfuran, methyl-4-nitrobutyrate, and acrolein after converting the nitro group into a ketone and a subsequent reductive amination.

    6. Aryne Chemistry

      Aryne Cycloaddition with Stable Münchnones: Synthesis of 9,10-Dihydro-9,10-epiminoanthracenes and Isoindoles (pages 55–57)

      Yuesi Fang, Prof. Richard C. Larock and Prof. Feng Shi

      Version of Record online: 20 NOV 2013 | DOI: 10.1002/ajoc.201300221

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      The münchies: Stable münchnones react with arynes under mild conditions to afford 1:1 and 1:2 adducts. The 1:1 adduct, an isoindole, is formed by a [3+2] cycloaddition/[4+2] cycloreversion sequence, while the 1:2 adduct, a 9,10-dihydro-9,10-epiminoanthracene, results from a further [4+2] cycloaddition with a second molecule of aryne. EWG= electron-withdrawing group.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Correction
    6. News
    7. Focus Review
    8. Communications
    9. Full Papers
    1. Total Synthesis

      Ring-Closing Metathesis Enabled Efficient Synthesis of γ-Butenolide Antifungal Agent (−)-Incrustoporin and its Analogues (pages 58–62)

      Prof. Rodney A. Fernandes, Pradnya H. Patil and Asim K. Chowdhury

      Version of Record online: 20 DEC 2013 | DOI: 10.1002/ajoc.201300216

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      Closed loop: The synthesis of (−)-incrustoporin and its analogues based on ring-closing metathesis has been achieved. The synthesis starts from various allyl alcohols and commercially available 2-arylacetic acids in four steps and 20-22 % overall yields.

    2. Electrophilic Spiroketalization

      Electrophile-Promoted Tandem Cyclization of α,β-Diynyl Ketodiols: A Facile Synthesis of Tetrahalogenated Spiroketals (pages 63–67)

      Dr. Hai-Tao Zhu, Jia Wang, Zi-Hang Qiu, Dr. Li-Jing Wang, Mei-Jin Zhong, Prof. Dr. Xue-Yuan Liu and Prof. Dr. Yong-Min Liang

      Version of Record online: 13 NOV 2013 | DOI: 10.1002/ajoc.201300202

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      Four! An efficient synthetic approach to tetrahalogenated spiroketals has been developed through a tandem iodocyclization of various α,β-diynyl ketodiols. The diastereoselective construction of a chiral spiroketal center induced by chiral alkynol functional groups is possible. Compounds with multiple aromatic substituents can be obtained by subsequent palladium-catalyzed coupling reactions of the resulting halides.

    3. C[BOND]H Activation

      Palladium-Catalyzed Aryl C[BOND]H Activation and Tandem ortho-Hydroxylation/Alkoxylation of 2-Aryl Benzimidazoles: Cytotoxicity and DNA-Binding Studies (pages 68–76)

      Ahmed Kamal, Vunnam Srinivasulu, Manda Sathish, Yellaiah Tangella, V. Lakshma Nayak, M. P. Narasimha Rao, Nagula Shankaraiah and Narayana Nagesh

      Version of Record online: 20 DEC 2013 | DOI: 10.1002/ajoc.201300214

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      Do it in tandem: An efficient regioselective aryl C[BOND]H activation and tandem o-hydroxylation/alkoxylation method for 2-aryl benzimidazoles has been developed using a Pd(OAc)2/oxone/Cs2CO3 catalytic system. Some of the compounds have significant IC50 values ranging from 1–10 μM in selected human cancer cell lines. The DNA-binding potential of the compounds was also investigated by UV/vis, fluorescence, and circular dichroism spectroscopy.

    4. Synthetic Methods

      Palladium-Catalyzed Odorless One-Pot Synthesis of Vinyl Sulfides from Organohalides, Thiourea, and Alkynes (pages 77–81)

      Jie Feng, Guoping Lu, Meifang Lv and Dr. Chun Cai

      Version of Record online: 13 JAN 2014 | DOI: 10.1002/ajoc.201300187

      Thumbnail image of graphical abstract

      Ode to odorless: The preparation of vinyl sulfides via a three-component reaction of halides, thiourea, and alkynes was reported. Two carbon-sulfur bonds were formed in one pot in this [Pd(dppf)Cl2] (dppf=1,1′-bis(diphenylphosphino)ferrocene) catalytic system. The protocol is free of foul-smelling thiols and operated under mild conditions to obtain cis-configured anti-Markovnikov products with moderate to excellent yields and excellent selectivity.

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