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2006 Fiscal Year Final Research Report Summary

Development of environmentally benign and highly active acid-base catalysts and their synthetic application

Research Project

Project/Area Number 15205021
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Environmental chemistry
Research InstitutionNagoya University

Principal Investigator

ISHIHARA Kazuaki  Nagoya University, Graduate School of Engineering, Professor (40221759)

Co-Investigator(Kenkyū-buntansha) SAKAKURA Akira  Nagoya University, EcoTopia Science Institute, Associate Professor (80334043)
HATANO Manabu  Nagoya University, Graduate School of Engineering, Lecturer (20362270)
Project Period (FY) 2003 – 2006
Keywordscatalysis / salt / conjugate / acid-base combination chemistry / asymmetric synthesis / artificial enzymes / hydrophobic effect / cation-π complex
Research Abstract

The design of small but highly functional artificial catalysts is very important for practical organic synthesis. We have succeeded in the rational design of small and simple catalysts and related reactions based on acid-base combination chemistry. Acid-base combined catalysts can be classified into three types: (1) acid-base combined salt catalysts (Type A), (2) conjugate acid-base catalysts (Type B), and (3) non-conjugate acid-base catalysts (Type C):
1. Acid-base combined salt catalysts (Type A)
1-1. Bronsted acid-base combined salt catalysts (Type A-1): bulky diarylammonium pentafluorobenzenesulfonates as mild and extremely active dehydrative ester condensation catalysts; chiral ammonium alkanesulfonates as asymmetric Diels-Alder catalysts
1-2. Lewis acid-base combined salt catalysts and reagents (Type A-2): magnesium ate complexes derived from Grignard reagents and alkyllithium as highly alkyl-selective reagents to ketones; zinc ate complexes as catalysts for the highly alkyl-selecti … More ve addition of Grignard reagents to ketones and aldimines
1-3. Cation-anion pair catalysts (Type A-3): lithium N, N-diisopropylamide in Haller-Bauer and Cannizzaro reactions; chiral lithium binaphtholate aqua complex as a highly effective asymmetric catalyst for trimethylsilylcyanation
1-4. Cation-a complex catalysts (Type A-4): chiral Cu(II)・L-DOPA-derived monopeptide complex as an asymmetric Diels-Alder and Mukaiyama-Michael catalyst
2. Lewis acid-base conjugate catalysts (Type B): molybdenum oxides as highly effective dehydrative cyclization catalysts directed toward the synthesis of oxazolines and thiazolines (Type B-1(monoconjugation)); zinc(II)・3,3'-diphosphinoyl-BINOLates in the asymmetric addition of organozinc reagents to aldehydes (Type B-2 (triconjugation))
3. Bronsted acid-Lewis base non-conjugate asymmetric catalysts (separated type) (Type C): L-histidine-derived sulfonamide as a minimal artificial acylase for the kinetic resolution of racemic alcohols
Thus, we developed new acid-base combined catalysts bearing excellent functions such as dual activation, control of nucleophilicity and basicity, asymmetric induction, hydrophobic effect, and so on. Current research is focused on the development of artificial highly functional catalysts which are superior to natural enzymes. Less

  • Research Products

    (55 results)

All 2007 2006

All Journal Article (45 results) Book (2 results) Patent(Industrial Property Rights) (8 results)

  • [Journal Article] Dimeric scandium(III)and monomeric lanthanide(III)complexes withperfluoropropane-l, 3-disulfonates as counter anions for Lewis acidcatalysis2007

    • Author(s)
      Manabu Hatano
    • Journal Title

      J. Organomet. Chem. 692・1-3

      Pages: 569-578

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Rhenium(VII) oxo complex-catalyzed direct condensation of phosphoric acid with nearly equimolar amounts of alcohols2007

    • Author(s)
      Akira Sakakura
    • Journal Title

      Angew. Chem. Int. Ed. 46・9

      Pages: 1423-1426

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Perrhenic acid-catalyzed dehydration from primary amides, aldoximes, N-monoacylureas, and α-substituted ketoximes to nitrile compounds2007

    • Author(s)
      Yoshiro Furuya
    • Journal Title

      Bull. Chem. Soc. Jpn. 80・2

      Pages: 400-406

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Biomimetic enantioselective halocyclization of polyprenoids inducedby nucleophilic phosphines2007

    • Author(s)
      Akira Sakakura
    • Journal Title

      Nature 455・7130

      Pages: 900-903

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Unusual rate-acceleration in the Bronsted acid-catalyzed dehydrationreactions : Local hydrophobic environment in aggregated N-(2, 6-diphenylphenyl)-N-mesitylammonium pentafluorobenzenesulfonates2007

    • Author(s)
      Akira Sakakura
    • Journal Title

      Chem. Asian J. 2・4

      Pages: 477-483

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Kinetic resolution of racemic alcohols catalyzed by minimal artificialacylases derived from L-histidine2007

    • Author(s)
      Yuji Kosugi
    • Journal Title

      Tetrahedron 63・28

      Pages: 6191-6203

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Dehydrative cyclizaion catalyzed by the combination ofmolybdenum(VI)oxides and benzoic acids : First synthesis of theantitumour substance BE-700162007

    • Author(s)
      Akira Sakakura
    • Journal Title

      Adv. Synth. Catal. 349・4-5

      Pages: 551-555

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] New boron(III)-catalyzed amide and ester condensation reactions2007

    • Author(s)
      Toshikatsu Maki
    • Journal Title

      Tetrahedron 63・35

      Pages: 8645-8657

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Catalytic synthesis of peptide-derived thiazolines and oxazolines using bis(quinolinolato)dioxomolybdenum(VI)complexes2007

    • Author(s)
      Akira Sakakura
    • Journal Title

      Adv. Synth. Catal. 349・10

      Pages: 1641-1646

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Recent progress in selective additions of organometal reagents to carbonyl compounds2007

    • Author(s)
      Manabu Hatano
    • Journal Title

      Current Organic Chemistry 11・2

      Pages: 127-157

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 究極のアルキル化剤の創製に挑む 効率的な第三級アルコール合成反応の開発2007

    • Author(s)
      波多野学, 鈴木伸治, 石原一彰
    • Journal Title

      化学 62・3

      Pages: 16-20

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Design of highly functional small-molecule catalysts and related reactions based on acid-base combination chemistry2007

    • Author(s)
      Kazuaki Ishihara
    • Journal Title

      Synlett 5

      Pages: 686-703

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Dimeric scandium(III) and monomeric lanthanide(III) complexes with perfluoropropane-l,3-disulfonates as counter anions for Lewis acid catalysis2007

    • Author(s)
      Manabu Hatano
    • Journal Title

      J. Organomet. Chem. 692・1-3

      Pages: 569-578

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Perrhenic acid-catalyzed dehydration from primary amides, aldoximes, N-monoacylureas, and a-substituted ketoximes to nitrile compounds2007

    • Author(s)
      Yoshiro Furuya
    • Journal Title

      Bull. Chem. Soc. Jpn. 80・2

      Pages: 400-406

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Biomimetic enantioselective halocyclization of polyprenoids induced by nucleophilic phosphines2007

    • Author(s)
      Akira Sakakura
    • Journal Title

      Nature 455・7130

      Pages: 900-903

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Unusual rate-acceleration in the Brensted acid-catalyzed dehydration reactions: Local hydrophobic environment in aggregated N-(2,6-diphenylphenyl)-N-mesitylammonium pentafluorobenzenesulfonates2007

    • Author(s)
      Akira Sakakura
    • Journal Title

      Chem. Asian J. 2・4

      Pages: 477-483

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Kinetic resolution of racemic alcohols catalyzed by minimal artificial acylases derived from L-histidine2007

    • Author(s)
      Yuji Kosugi
    • Journal Title

      Tetrahedron 63・28

      Pages: 6191-6203

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Dehydrative cyclizaion catalyzed by the combination of molybdenum(VI) oxides and benzoic acids: First synthesis of the antitumour substance BE-700162007

    • Author(s)
      Akira Sakakura
    • Journal Title

      Adv. Synth. Catal. 349・4-5

      Pages: 551-555

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Catalytic synthesis of peptide-derived thiazolines and oxazolines using bis(quinolinolato)dioxomolybdenum(VI) complexes2007

    • Author(s)
      Akira Sakakura
    • Journal Title

      Adv. Synth. Catal. 349・10

      Pages: 1641-1646

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Design of ultimate alkylating reagents: Development of highly efficient reaction to synthesize tertiary alcohols2007

    • Author(s)
      Manabu Hatano
    • Journal Title

      Kagaku 62・3

      Pages: 16-20

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Design of highly functional small-molecule catalysts and related reactions based on acid-base combination chemistry2007

    • Author(s)
      Kazuaki Ishihara
    • Journal Title

      Synlett -・5

      Pages: 686-703

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Crucial role for the conjugate base for silyl Lewis acid-induced Mukaiyama aldol reaction2006

    • Author(s)
      Yukihiro Hiraiwa
    • Journal Title

      Eur. J. Org. Chem. 8

      Pages: 1837-1844

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 4, 5, 6, 7-Tetrachloro[d][1, 3, 2]dioxaborol-2-ol as an effective catalystfor the amide condensation of sterically demanding carboxylic acids2006

    • Author(s)
      Toshikatsu Maki
    • Journal Title

      Org. Lett. 8・7

      Pages: 1431-1434

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Design of a small-molecule catalyst using intramolecular cation一πinteraction for enantioselective Diels-Alder and Mukaiyama-Michaelreactions : L-DOPA-derived monopeptide・Cu(II) complex2006

    • Author(s)
      Kazuaki Ishihara
    • Journal Title

      Org. Lett. 8・9

      Pages: 1921-1924

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Chiral 1, 1 '-binaphthy1-2, 2'-diammonium salt catalysts for theenantioselective Diels-Alder reaction with α-acyloxyacroleins2006

    • Author(s)
      Akira Sakakura
    • Journal Title

      Org. Lett. 8・11

      Pages: 2229-2232

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enantioselective dialkylzinc addition to aldehydes catalyzed by chiral Zn(II)-BINOLates bearing phosphonates and phosphoramides in the 3, 3'-positions2006

    • Author(s)
      Manabu Hatano
    • Journal Title

      Synlett 11

      Pages: 1762-1764

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Design of Bronsted acid-assisted chiral Bronsted acid (Chiral BBA)catalyst bearing a bis(triflyl)methyl group for a Mannich-type reaction2006

    • Author(s)
      Aiko Hasegawa
    • Journal Title

      Org. Lett. 8・15

      Pages: 3175-3178

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 3, 3'-Diphosphoryl-1, 1'-bi-2-naphthol-Zn(II)complexes as conjugateacid-base catalysts for enantioselective dialkylzinc addition toaldehydes2006

    • Author(s)
      Manabu Hatano
    • Journal Title

      J. Org. Chem. 71・17

      Pages: 6474-6484

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Highly efficient alkylation to ketones and aldimines with Grignardreagents catalyzed by zinc(II) chloride2006

    • Author(s)
      Manabu Hatano
    • Journal Title

      J. Am. Chem. Soc. 128・31

      Pages: 9998-9999

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Iron(III)-zirconium(IV) combined salt immobilized on N-(polystyrylbutyl)pyridinium triflylimide as a reusable catalyst for a dehydrative esterification reaction2006

    • Author(s)
      Yuka Nakamura
    • Journal Title

      Adv. Synth. Catal 348・16-17

      Pages: 2457-2465

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 疎水機能をもつエステル脱水縮合触媒の設計2006

    • Author(s)
      石原一彰
    • Journal Title

      化学工業 57・6

      Pages: 426-430

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 低環境負荷型触媒的脱水反応プロセスの開発2006

    • Author(s)
      坂倉彰
    • Journal Title

      有機合成化学協会誌 64・6

      Pages: 651-663

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 第三級アルコール合成のブークスルー -アート錯体を用いたケトンヘのGrignard試薬の高効率的付加反応2006

    • Author(s)
      波多野学
    • Journal Title

      化学 61・11

      Pages: 68-69

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Crucial role for the conjugate base for silyl Lewis acid-induced Mukaiyama aldol reaction2006

    • Author(s)
      Yukihiro Hiraiwa
    • Journal Title

      Eur. J. Org. Chem. -・8

      Pages: 1837-1844

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] 4,5,6,7-Tetrachloro[d][l,3,2]dioxaborol-2-ol as an effective catalyst for the amide condensation of sterically demanding carboxylic acids2006

    • Author(s)
      Toshikatsu Maki
    • Journal Title

      Org. Lett. 8・7

      Pages: 1431-1434

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Design of a small-molecule catalyst using intramolecular cation-π interaction for enantioselective Diels-Alder and Mukaiyama-Michael reactions: L-DOPA-derived monopeptide・Cu(II) complex2006

    • Author(s)
      Kazuaki Ishihara
    • Journal Title

      Org. Lett. 8・9

      Pages: 1921-1924

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Chiral 1,1'-binaphthyl-2,2'-diammonium salt catalysts for the enantioselective Diels-Alder reaction with a-acyloxyacroleins2006

    • Author(s)
      Akira Sakakura
    • Journal Title

      Org. Lett. 8・11

      Pages: 2229-2232

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enantioselective dialkylzinc addition to aldehydes catalyzed by chiral Zn(II)-BINOLates bearing phosphonates and phosphoramides in the 3,3' -positions2006

    • Author(s)
      Manabu Hatano
    • Journal Title

      Synlett -・11

      Pages: 1762-1764

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Design of Bronsted acid-assisted chiral Bronsted acid (Chiral BBA) catalyst bearing a bis(triflyl)methyl group for a Mannich-type reaction2006

    • Author(s)
      Aiko Hasegawa
    • Journal Title

      Org. Lett. 8・15

      Pages: 3175-3178

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] 3,3' -Diphosphoryl-1,1' -bi-2-naphthol-Zn(II) complexes asconjugate acid-base catalysts for enantioselective dialkylzinc addition to aldehydes2006

    • Author(s)
      Manabu Hatano
    • Journal Title

      J. Org. Chem. 71・17

      Pages: 6474-6484

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Highly efficient alkylation to ketones and aldimines with Grignard reagents catalyzed by zinc(II) chloride2006

    • Author(s)
      Manabu Hatano
    • Journal Title

      J. Am. Chem. Soc. 128・31

      Pages: 9998-9999

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Iron(III)-zirconium(IV) combined salt immobilized on N-(polystyrylbutyl)pyridinium triflylimide as a reusable catalyst for a dehydrative esterification reaction2006

    • Author(s)
      Yuka Nakamura
    • Journal Title

      Adv. Synth. Catal. 348・16-17

      Pages: 2457-2465

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Design of dehydrative ester condensation catalysts bearing hydrophobic functions2006

    • Author(s)
      Kazuaki Ishihara
    • Journal Title

      Kagakukougyou 57・6

      Pages: 426-430

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Development of environmentally benign catalytic dehydration process2006

    • Author(s)
      Akira Sakakura
    • Journal Title

      J. Org. Synth. Chem. 64・6

      Pages: 651-663

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Breakthough for synthesis of tertary alcohols: highly efficient addition of Grignard reagents to ketones through ate complexes2006

    • Author(s)
      Manabu Hatano
    • Journal Title

      Kagaku 61・11

      Pages: 68-69

    • Description
      「研究成果報告書概要(欧文)」より
  • [Book] 自然に学ぶ材料プロセツシンダの創成2007

    • Author(s)
      浅井滋生
    • Total Pages
      370
    • Publisher
      三共出版
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] Nature-guided materials processing2007

    • Author(s)
      Shigeo Asai
    • Total Pages
      370
    • Publisher
      Sankyo Publishing
    • Description
      「研究成果報告書概要(欧文)」より
  • [Patent(Industrial Property Rights)] 有機金属複合体及びアルドール付加体の製造方法2007

    • Inventor(s)
      石 原 一彰, 波多野 学
    • Industrial Property Rights Holder
      国立大学法人名古屋大学
    • Industrial Property Number
      特願2007-018431
    • Filing Date
      2007-01-29
    • Description
      「研究成果報告書概要(和文)」より
  • [Patent(Industrial Property Rights)] ラウロラクタムの製造方法2007

    • Inventor(s)
      石 原 一彰, 釘本純一, 河井譲治
    • Industrial Property Rights Holder
      国立大学法人名古屋大学, 宇部興産株式会社
    • Industrial Property Number
      特願2007-30474
    • Filing Date
      2007-02-09
    • Description
      「研究成果報告書概要(和文)」より
  • [Patent(Industrial Property Rights)] リン酸エステルの製造方法2007

    • Inventor(s)
      石 原 一彰, 坂倉彰, 勝川幹基, 井上佳尚
    • Industrial Property Rights Holder
      国立大学法人名古屋大学, 三井化学
    • Industrial Property Number
      特願2007-042875
    • Filing Date
      2007-02-22
    • Description
      「研究成果報告書概要(和文)」より
  • [Patent(Industrial Property Rights)] ホスホロアミド化合物及びその製造方法、配位子、錯体、触媒、及び光学活性アルコールの製造方法2007

    • Inventor(s)
      石 原 一彰, 波多野 学, 宮本隆史
    • Industrial Property Rights Holder
      国立大学法人名古屋大学
    • Industrial Property Number
      特願2007-61030
    • Filing Date
      2007-03-09
    • Description
      「研究成果報告書概要(和文)」より
  • [Patent(Industrial Property Rights)] エステル合成触媒及びエステルの製造方法2007

    • Inventor(s)
      石原一彰
    • Industrial Property Rights Holder
      国立大学法人名古屋大学
    • Industrial Property Number
      特願2007-080053
    • Filing Date
      2007-03-26
    • Description
      「研究成果報告書概要(和文)」より
  • [Patent(Industrial Property Rights)] カルボニル化合物の製造方法2007

    • Inventor(s)
      石 原 一彰 Muhammet Uyanik
    • Industrial Property Rights Holder
      国立大学法人名古屋大学
    • Industrial Property Number
      特願2007-094377
    • Filing Date
      2007-03-30
    • Description
      「研究成果報告書概要(和文)」より
  • [Patent(Industrial Property Rights)] 錯体、エステル合成用触媒及びエステルの製造方法2007

    • Inventor(s)
      石 原 一彰, 古家吉朗
    • Industrial Property Rights Holder
      国立大学法人名古屋大学
    • Industrial Property Number
      特願2007-094378
    • Filing Date
      2007-03-30
    • Description
      「研究成果報告書概要(和文)」より
  • [Patent(Industrial Property Rights)] 亜鉛-マグネシウムアート錯体を含む求核試薬及びそれを使用する求核付加体の製造方法2006

    • Inventor(s)
      石原 一彰, 波多野 学
    • Industrial Property Rights Holder
      国立大学法人名古屋大学
    • Industrial Property Number
      特願2006-117688
    • Filing Date
      2006-04-21
    • Description
      「研究成果報告書概要(和文)」より

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Published: 2010-06-09  

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