Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
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Volume 70, Issue 6
Displaying 1-11 of 11 articles from this issue
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Preface
Reviews and Accounts
  • Development of π-Acidic Metal-Catalyzed Reactions toward Construction of Multi-Substituted Heterocycles
    Itaru Nakamura
    2012 Volume 70 Issue 6 Pages 581-592
    Published: June 01, 2012
    Released on J-STAGE: July 02, 2012
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.70.581
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    π-Acidic metal-catalyzed cyclization reaction is one of the most efficient methods to construct highly elaborate molecular skeletons in a single operation under mild reaction conditions. These transformations often involve cleavage of σ bonds. Investigations into catalytic skeletal rearrangement have mainly utilized alkynylamines, alkynylalcohols, enynes, and propargylic esters as substrates. In this article, I report our recent findings on π-acidic metal-catalyzed reactions via cleavage of σ bonds between major elements in body, such as carbon, nitrogen, oxygen, and sulfur, producing multisubstituted heterocycles in an atom-efficient manner. That is, (a) catalytic carbon-heteroatom bond addition of ortho-alkynylphenyl ethers, -anilines, and -phenyl sulfides and (b) catalytic skeletal rearrangement of O-propargylic oximes.
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  • Catalytic Asymmetric Synthesis of Planar-Chiral Transition-Metal Complexes
    Sachie Arae, Masamichi Ogasawara
    2012 Volume 70 Issue 6 Pages 593-605
    Published: June 01, 2012
    Released on J-STAGE: July 02, 2012
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.70.593
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    Although “central chirality” based on stereogenic carbon atoms is arguably the most common chiral element in organic chemistry, chiral molecules devoid of stereogenic centers play important roles in stereoselective organic transformations. Among these chiral compounds with “non-centrochirality”, planar-chiral transition-metal complexes have been utilized as chiral ligands, chiral catalysts, or chiral building blocks in asymmetric synthesis. However, enantiomerically enriched forms of these compounds are primarily obtained by rather classical methods. Examples of catalytic enantioselective induction of planar-chirality in transition-metal species have been extremely rare and still a developing area in this field. In this review article, catalytic asymmetric synthesis of various “planar-chiral transition-metal complexes” are surveyed in a comprehensive manner.
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  • Molecular Conversion of Conjugated Polymers via Electron-Transfer on Electrode as a Key Step
    Shinsuke Inagi, Toshio Fuchigami
    2012 Volume 70 Issue 6 Pages 606-614
    Published: June 01, 2012
    Released on J-STAGE: July 02, 2012
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.70.606
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    Electron-transfer behaviors of conjugated polymers on electrode (electrochemical doping) have been studied well for the purpose of electrochemical device applications such as conducting material and electrochromic material. In this study, we treated a charged (doped) state of conjugated polymers as an intermediate for following chemical reactions based on the concept of electroorganic synthesis. The post-functionalization of conjugated polymers was successfully achieved when a reactive dopant (conter ion derived from electrolyte) was used for the electrochemical reactions. For example, the polymer reactions such as anodic halogenations, cathodic reduction, and gradient oxidation reaction on bipolar electrode were successfully carried out to tune the optical and electrochemical properties of the polymers.
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  • Synthesis of Marine Natural Product Agelastatin A
    Tomonori Yamaoka, Yoshiyasu Ichikawa, Hiyoshizo Kotsuki
    2012 Volume 70 Issue 6 Pages 615-628
    Published: June 01, 2012
    Released on J-STAGE: July 02, 2012
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.70.615
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    Pietra and co-workers reported isolation of (−)-agelastatins A and B from the deep water marine sponge Agelas dendromorpha collected in the Coral Sea near New Caledonia. The structure of these alkaloids featuring the architecturally unique tetracyclic array, coupled with their significant biological activity and scarce availability from marine organisms, has stimulated the synthetic community, resulting in inventive syntheses from eleven different research groups. In this review, these synthetic studies of agelastatin A showcasing elegant and powerful modern synthetic methodologies, are summarized.
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  • Synthesis of Chain Type and Fused π-Conjugated Phosphole Derivatives
    Yoshihiro Matano, Hiroshi Imahori
    2012 Volume 70 Issue 6 Pages 629-639
    Published: June 01, 2012
    Released on J-STAGE: July 02, 2012
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.70.629
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    Phosphole has a low aromaticity and exhibits characteristic optical and electrochemical properties derived from the phosphorus-bridged 1,3-diene π system. In addition, phosphole has an active lone pair at phosphorus. The most remarkable feature of the phosphole-based π-systems is that their fundamental properties are tunable by chemical functionalizations at the phosphorus center. In this regard, phosphole-based π-systems are now regarded as one of the future materials for use in optoelectronics. In this article, we would like to briefly summarize our recent results on the synthesis of novel π-conjugated phosphole derivatives with representative examples, which contain phosphole-vinylene, phosphole-acetylene, phosphole-heterole, phosphole-benzene, phosphole-phosphole, benzo[c]phosphole, acenaphtho[c]phoshole, and diacenaphtho[b,d]phosphole skeletons. The target compounds were successfully prepared by two main approaches, titanacycle method and Stille coupling. Selected structural, optical, and electrochemical data for a few derivatives are also presented. The results described herein would give valuable information and guidelines for designing phosphole-based opto-electrochemical materials.
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  • Chirality Sensing based on Changes in Conformation of Dynamic Terephthalamide Hosts: Propeller-, Double-arm-, and Figure-of-eight-shaped Hosts
    Ryo Katoono, Hidetoshi Kawai, Kenshu Fujiwara, Takanori Suzuki
    2012 Volume 70 Issue 6 Pages 640-650
    Published: June 01, 2012
    Released on J-STAGE: July 02, 2012
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.70.640
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    This article describes the chirality sensing systems based on changes in conformation of dynamic terephthalamide hosts from a nonhelical form to a helical form with biasing to prefer one handedness upon complexation with a chiral guest through supramolecular transmission of chirality. The syn form is endowed with the ability to capture a ditopic guest through hydrogen bonds at the amide carbonyls; thus in a complexed state, a strong CD signal is produced thanks to a helical conformation induced by the conformational change and a biased handedness. Attachment of chirality to the terephthalamide host itself leads to an intrinsic preference in the sense of dynamic helicity in a helical syn form. Cooperative transmission of chiralities within the host and from the guest enables to further design an advanced sensing system with stereospecific chiroptical modulation, based on a stereospecific change in conformation of the chiral dynamic host upon complexation with a pair of enantiomeric guests.
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Review de Debut
  • SN2 Reaction on Vinylic Carbon
    Hiromichi Egami
    2012 Volume 70 Issue 6 Pages 651-652
    Published: June 01, 2012
    Released on J-STAGE: July 02, 2012
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.70.651
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    Even in recent days, the SN2 reaction on vinylic carbons is not very common. This reaction pathway has been considered as an unlikely mechanism for a long time. However, recent investigations clearly indicate that nucleophilic attack on the σ* orbital of Csp2-LG bond is viable. In this short review, representative examples of this type of reaction are outlined.
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  • Porous Organic Cage Crystals
    Kosuke Ono
    2012 Volume 70 Issue 6 Pages 653-654
    Published: June 01, 2012
    Released on J-STAGE: July 02, 2012
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.70.653
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    Nanoporous materials are important in applications such as molecular separations, catalysts and gas storage. Metal-organic frameworks (MOFs), covalent organic frameworks (COFs), and nanoporous polymers have dominated this research area. By contrast, discrete organic molecules tend to pack efficiently in solid state, leaving as little empty space as possible, which leads to non-porous materials. This review will highlight the recent developments with discrete organic cage molecules that are porous in solid state.
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