Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
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Volume 56, Issue 1
Displaying 1-9 of 9 articles from this issue
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  • Solid Phase Synthesis of Heterocyclic Compounds
    Yoshinori KONDO, Hisashi SHINKAI, Ken-ichi TANJI
    1998 Volume 56 Issue 1 Pages 2-10
    Published: January 01, 1998
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.56.2
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    Recent developments and current situation of solid phase heterocyclic synthesis are discussed focussing on cyclization of heterocyclic compounds. Solid phase synthesis is regarded as a basic technology for supporting combinatorial synthesis and automated synthesis. Heterocyclic compounds have been found in many biologically active substances and further investigation of solid phase heterocyclic chemistry is desired.
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  • Development of the Asymmetric Cycloaddition Reactions and Asymmetric Nucleophilic Addition Reaction Utilizing Tartaric Acid Esters
    Katsuhiko INOMATA, Yutaka UKAJI
    1998 Volume 56 Issue 1 Pages 11-21
    Published: January 01, 1998
    Released on J-STAGE: January 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.56.11
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    In order to develop a practical method for the construction of chiral molecules, we have designed a novel chiral system possessing two metal centers utilizing tartaric acid esters : that is, if two reactants are bound to the two metal centers of a dialkoxide derived from tartaric acid ester, they might be ideally oriented and/or activated by the metals and the subsequent reaction can proceed in an enantioselective manner to afford the corresponding optically active products. According to this working hypothesis, we could develop an asymmetric Simmons-Smith reaction, asymmetric 1, 3-dipolar cycloaddition reactions of nitrile oxides and nitrones, and an asymmetric nucleophilic addition reaction of dialkylzincs to nitrones.
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  • New Enantiomeric Resolution Phenomenon of Racemic Crystals : Preferential Enrichment
    Rui TAMURA, Hiroki TAKAHASHI, Takanori USHIO
    1998 Volume 56 Issue 1 Pages 22-33
    Published: January 01, 1998
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.56.22
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    We have discovered the first case of accomplishment of an enantiomeric resolution by simple recrystallization of a series of racemic compounds [(±) forms] composed of a regular packing of (+) and (-) molecules in a crystal, although in principle this sort of enantiomeric resolution has been considered to be infeasible for more than a century since the discovery of chiral crystals by Pasteur and preferential crystallization of conglomerates by Gernetz which are a mixture of homochiral (+) and (-) crystals. We have designated this new enantiomeric resolution phenomenon as “Preferential Enrichment”. Here we report a distinct evidence that polymorphism between a racemic compound and a mixed crystal (solid solution), which consists of alternating alignment of the two homochiral dimers in a crystal, is responsible for the “Preferential Enrichment”, and we propose a mechanism of the phenomenon of the reversal of chirality in the deposited crystals, that is the essence of the “Preferential Enrichment”, on the basis of the polymorphic transformation during crystallization.
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  • Palladium (II) -catalyzed Cyclization via N-Alkylation of an Allyl Alcohol by a Urethane and Its Application to the Syntheses of Natural Products
    Yoshiro HIRAI, Hajime YOKOYAMA
    1998 Volume 56 Issue 1 Pages 34-44
    Published: January 01, 1998
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.56.34
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    Stereoselective amino-cycloaddition of alkenylamines is one of the most important approaches for the stereoselective construction of nitrogen hetero-alicycles, which form the skeletons of several bio-logically active natural products and related compounds. We recently developed the intramolecular substitution of an allylic alcohol by a heteroatom using a palladium (II) catalyst without activation of the allylic alcohol. This review describes the stereoselective cyclization of the optically active urethanes and oxazolidinones containing allyl alcohol moiety using bis (acetonitrile) palladium (II) chloride leading to the 2-functionalized 5-hydroxypiperidine, the trans-2, 5-disubstituted pyrrolidine, and the trans -2, 6-piperidine, respectively. The stereoselective construction of different stereoisomers from similar precursors by changing transition metals (a palladium (II) catalyst → a silver salt) is also described.
    The cyclo-adducts obtained were proved to be useful chiral building blocks by their conversion into (+) -coniine, (-) -5-hydroxysedamine, (-) -bulgecinine, (+) -prosopinine, and a prospective synthetic intermediate of (+) -palustrine, respectively.
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  • Recent Developments of Arylboron Compounds as Lewis Acid Catalysts
    Hideki KURIHARA, Kazuaki ISHIHARA, Hisashi YAMAMOTO
    1998 Volume 56 Issue 1 Pages 45-53
    Published: January 01, 1998
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.56.45
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    Arylboron compounds with electron-withdrawing substituents at their aryl groups are water tolerant Lewis acid catalysts for various carbon-carbon bond formation reactions. For examples, tris (pentafluorophenyl)boron catalyzes aldol-type reaction of aldehydes and imines with silyl enol ethers, stereoselective rearrangement of epoxides, hydrosilation of carbonyl compounds, etc. 3, 4, 5-Trifluorophenylboronic acid promotes amidation reaction between carboxylic acids and amines. Bis (pentafluorophenyl) borinic acid catalyzes substrate selective dehydration reaction of anti-aldols, and Oppenauer oxidation of allylic, and benzylic alcohols.
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  • Living Polymerizations by Non-metallocene Type Complexes
    Hajime YASUDA
    1998 Volume 56 Issue 1 Pages 54-63
    Published: January 01, 1998
    Released on J-STAGE: January 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.56.54
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    This article describes the recent development in the field of polymerizations of polar and nonpolar monomers catalyzed by non-metallocene type initiators. Brookhart discovered block copolymerization of ethylene with alkyl acrylate and also linear polymerization of 1-olefins with Ni or Pd diimide complexes. Living polymerization of 1-olefins was achieved for the first time using Ti-amide complexes by Scollard. The polymerization of methyl methacrylate by Yb [C (SiMe3) 3] 2 produced high molecular weight polymers (Mn>200 × 103) with very narrow molecular weight distribution (Mw/Mn=1.1) and high isotacticity (97%). As a consequence, stereo-complex was obtained by mixing the isotactic polymer with highly syndiotactic poly (methyl methacrylate) synthesized by [Cp2*SmH] 2. As a polar monomer, an alkyl isocyanate was polymerized by TiC13OCH2CF3 by Novak. Polymerizations of acetylenes and conjugated dienes were realized using rare earth metal complexes.
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  • A Case History in Chemical Research : Some Aspects of Organosilicon and Ferrocene Chemistry and Asymmetric Synthesis
    Makoto KUMADA
    1998 Volume 56 Issue 1 Pages 64-70
    Published: January 01, 1998
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.56.64
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  • Ytterbium (III) Trifluoromethanesulfonate
    Tadayoshi OGINO, Takashi ONOZAWA
    1998 Volume 56 Issue 1 Pages 71-73
    Published: January 01, 1998
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.56.71
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  • [title in Japanese]
    [in Japanese], [in Japanese], [in Japanese], [in Japanese], [in Japane ...
    1998 Volume 56 Issue 1 Pages 74
    Published: January 01, 1998
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.56.74
    JOURNAL FREE ACCESS
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