Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
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Volume 68, Issue 10
Displaying 1-13 of 13 articles from this issue
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Preface
Reviews and Accounts
  • New Synthetic Reactions Using Conjugate Addition Reactions of Nucleophiles to α,β-Unsaturated Imines
    Iwao Hachiya, Makoto Shimizu
    2010 Volume 68 Issue 10 Pages 1006-1016
    Published: October 01, 2010
    Released on J-STAGE: November 08, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.68.1006
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    The development of a new efficient synthetic method of nitrogen containing compounds is extensively studied because there are many nitrogen containing compounds such as amino acids, alkaloids, and β-lactams having biological activities and functionalized materials for organic electronics or photonics. During the investigation of Mannich-type reactions of α,β-unsaturated imines with ketene silyl acetals, we found that 1,4-and 1,2-double nucleophilic addition reactions proceeded to give doubly alkylated products in good yields. Various nucleophiles can be also used such as allyltins, ketene silyl thio acetals, trimethylsilyl cyanide, thiols, and hydrogen azide. Using 1,4-and 1,2-double nucleophilic addition reactions with ketene silyl acetal and trimethylsilyl cyanide as a key reaction, an imidazole glycerol phosphate dehydratase inhibitor(IGPDI) possessing a monopyrrole aldehyde moiety is synthesized. 2-Iminopyridine synthesis is found in the conjugate addition of cyanoacetate derivatives to alkynyl imines. Stereodivergent synthesis of both cis-and trans-β-lactams is presented using the following three reactions: Iminocyclobutenone formation, chemoselective reduction of imino groups, and thermal rearrangement of aminocyclobutenones as crucial steps, in which the starting materials, iminocyclobutenones, were readily synthesized using conjugate addition reactions of alkynyl imines with ketene silyl acetals in good yields.
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  • Asymmetric Syntheses Using Heteroarenesulfonyl Groups as a Highly Functional Protecting-activating Group
    Shuichi Nakamura, Norio Shibata, Takeshi Toru
    2010 Volume 68 Issue 10 Pages 1017-1027
    Published: October 01, 2010
    Released on J-STAGE: November 08, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.68.1017
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    Enantioselective bond formation reaction is of great interest to medicinal or material science. In order to develop the synthetic methodology for these compounds, we designed heteroarenesulfonyl groups as an activating group for imines and a protecting group for amines. The heteroarenesulfonyl group was shown to be an efficient protective group, which has notable properties of high chiral inducibility and activation of the imino group toward the addition of several nucleophiles. Furthermore, we designed N-(heteroarenesulfonyl)prolinamides as novel organocatalysts. Enantioselective aldol reaction of acetone or acetaldehyde with various isatin derivatives using N-(2-thiophenesulfonyl)prolinamide afforded convolutamydine derivatives with high enantioselectivity.
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  • Hydrogen-transfer Oxidation Using Iridium Amide Complex and Their Application to Asymmetric Synthesis
    Takeyuki Suzuki
    2010 Volume 68 Issue 10 Pages 1028-1035
    Published: October 01, 2010
    Released on J-STAGE: November 08, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.68.1028
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    This article describes several hydrogen transfer oxidation by an iridium amide catalyst. Oxidative lactonization, oxidative dimerization, and Oppenauer type-oxidation proceed by a novel iridium aminoalkoxide complex in ketonic solvent. Asymmetric oxidative lactonization and oxidative desymmetrization developed in this study were found to be useful for bioactive compound synthesis.
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  • Total Syntheses of Nitrogen-Containing Cyclic Natural Products Based on Aryl Amination
    Kentaro Okano, Tohru Fukuyama, Hidetoshi Tokuyama
    2010 Volume 68 Issue 10 Pages 1036-1046
    Published: October 01, 2010
    Released on J-STAGE: November 08, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.68.1036
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    This article focuses on the development of an aromatic amination reaction using CuI and CsOAc and its application to total syntheses of nitrogen-containing cyclic natural products. The reaction conditions present several unprecedented features that have not been observed in conventional palladium-catalyzed systems, including high functional group compatibility (e.g., N-alloc-and sp2-Br are retained) and applicability for highly hindered substrates. The utility of this reaction has been fully demonstrated through total syntheses of duocarmycins, yatakemycin, and PDE-II.
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  • Generation and Control of Chirality by Crystallization: Asymmetric Synthesis Using the Crystal Chirality in Fluid Media
    Masami Sakamoto, Takashi Mino, Tsutomu Fujita
    2010 Volume 68 Issue 10 Pages 1047-1056
    Published: October 01, 2010
    Released on J-STAGE: November 08, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.68.1047
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    Many examples of solid-state photoreactions using chiral crystals composed of achiral materials and leading to optically active products have been successfully demonstrated and recognized as absolute asymmetric synthesis. Recently, we have discovered a new methodology for asymmetric synthesis using the molecular chirality in crystal as a source of homochirality in fluid media. The chirality can be effectively transferred to optically active products by asymmetric reactions involving nucleophilic reactions and an intermolecular photochemical reaction, and which had so far not been achieved in solid state reactions.
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  • Modular Synthesis of Organic Electronic Materials
    Hayato Tsuji
    2010 Volume 68 Issue 10 Pages 1057-1066
    Published: October 01, 2010
    Released on J-STAGE: November 08, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.68.1057
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    We have been exploring new organic reactions and new class of organic functional materials based on the concept of “modular synthesis.” This manuscript presents our recent progress on the synthesis of a series of fused carbo- and heteroaromatic compounds by means of the development of intramolecular cyclization reaction. Utility of these new materials in organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic solar cells, is also demonstrated.
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