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Typical Metal-Catalyzed Asymmetric Synthesis

Research Project

Project/Area Number 05234105
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Research InstitutionNagoya University

Principal Investigator

YAMAMOTO Hisashi  Nagoya University, Graduate School of Engineering, Professor, 工学部, 教授 (10135311)

Co-Investigator(Kenkyū-buntansha) NAKAI Takeshi  Tokyo Institute of Technology, Department of Chemical Technology, Professor, 工学部, 教授 (90016717)
TAMAO Kouhei  Kyoto University, Institute for Chemical Research, Professor, 化学研究所, 教授 (60026218)
SUZUKI Keisuke  Keio University, Department of Chemistry, Professor, 理工学部, 教授 (90162940)
SHIOIRI Takayuki  Nagoya City University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (20012627)
OGUNI Nobuki  Yamaguchi University, Faculty of Science, Professor, 理学部, 教授 (60028165)
Project Period (FY) 1993 – 1995
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥95,500,000 (Direct Cost: ¥95,500,000)
Fiscal Year 1995: ¥27,900,000 (Direct Cost: ¥27,900,000)
Fiscal Year 1994: ¥32,700,000 (Direct Cost: ¥32,700,000)
Fiscal Year 1993: ¥34,900,000 (Direct Cost: ¥34,900,000)
Keywordstypical metal-catalyzed asymmetric synthesis / asymmetric Diels-Alder reaction / asymmetric protonation / asymmetric addition-ring opening reaction / chiral quaternary salt / stereospecific 1,2-rearrangement / asymmetric intramolecular hydrosilation / asymmetric allylation / 触媒的不斉プロトン化反応 / キラルシッフ塩基-チタン錯体 / テトラフェニルホスホニウムハイドロジエンジフルオリド / フラキノシンの全合成 / 触媒的不斉分子内ヒドロシリル化 / 不斉触媒付加反応 / 不斉触媒アリル化反応 / ルイス酸複合型キラルブレンステッド酸 / エナンチオ選択的プロトン化反応 / 光学活性シッフ塩基チタン錯体 / キラル4級アンモニウムフルオリド / アルキニル基の不斉1,2-転位 / 不斉チタン触媒 / キラルアシロキシボラン / キラルルイス酸 / シッフ塩基チタン錯体 / キラル相間移動触媒 / アノマー安定化効果 / ケイ素系不斉触媒反応 / 触媒的立体制御
Research Abstract

Asymmetric synthesis has developed rapidly and extensively, and is now growing into a new way of producing optically active chiral compounds that is more general and efficient than enzymatic reactions in many cases. The aim of project "typical metal-catalyzed asymmetric synthesis, " was executed by many organic chemists diving into six research groups of "development and application of designer Lewis acid (Yamamoto), " "asymmetric reactions of diketene with aldehydes catalyzed by chiral Schiff base-titanium complexes (Oguni), " "asymmetric synthesis utilizing chiral quaternary salt catalysts and chiral auxiliaries from monoterpenes (Shioiri), " "some new ways of organometallicbased stereocontrol (Suzuki), " "asymmetric intramolecular hydrosilation (Tamao), " and "development of catalytic asymmetric reactions (Nakai)" for three years beginning in 1993. This project was not only create various new asymmetric reactions by taking advantage of characteristics of typical elements, but also to apply many enantio- and diastereoselective reactions to the synthesis of the complex multi-chiral compounds including useful natural products. During 1993-1995, many new asymmetric or stereoselective reactions related to Diels-Alder reaction (Yamamoto), protonation (Yamamoto), addition-ring opening reaction of diketenes with aldehydes (Oguni), aldol reaction (Shioiri), addition of silylacetylenes to carbonyl compounds (Shioiri), 1,2-rearrangement of alkynyl groups (Suzuki), metallo-ene reaction (Suzuki), intramolecular hydrosilation (Tamao), addition of aldehydes with diethylzinc (Nakai), and allylation (Nakai) were developed.

Report

(4 results)
  • 1996 Final Research Report Summary
  • 1995 Annual Research Report
  • 1994 Annual Research Report
  • 1993 Annual Research Report
  • Research Products

    (37 results)

All Other

All Publications (37 results)

  • [Publications] H.Yamamoto: "First Example of a Highly Enantioselective Catalytic Protonation of Silyl Enol Ethers." J.Am.Chem.Soc.118. 12854-12855 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] N.Oguni: "Highly Efficient Preparation of Optically Active 5-Hydroxy-3-oxoesters by Enantioselective Reaction of Diketene with Aldehydes Promoted by Novel Chiral Sciff Base-Titanium Alkoxide Complexes." Tetrahedron Asymmetry. 6. 1833-1836 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shioiri: "Tetrahenylphosphonium Hydrogendifluoride:A New Catalyst for Silyl-mediated Aldol Reaction and the Addition of Silylacetylenes to Carbonyl Compounds" Synlett. 1033-1034 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Suzuki: "Total Synthesis of(+/-)-Furaquinocin D." J.Am.Chem.Soc.117. 10757-10758 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Tamao: "Silyl Anions" Adv.Organomet.Chem.38. 1-58 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Nakai: "Asymmetric Catalysis by a New Type of Chiral Binaphthol-Titanium Complex" Tetrahedron Lett.36. 1861-1864 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Yamamoto: "Advances in Catalytic Processes,Volume 1" JAI Press Inc., 194(31) (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Nakai: "Advances in Catalytic Processes,Volume 1" JAI Press Inc., 194(26) (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Yamamoto: "First Example of a Highly Enantioselective Catalytic Protonation of Silyl Enol Ethers." J.Am.Chem.Soc.118. 12854-12855 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] N.Oguni: "Highly Efficient Preparation of Optically Active 5-Hydroxy-3-oxoesters by Enantioselective Reaction of Diketene with Aldehydes Promoted by Novel Chiral Sciff Base-Titanium Alkoxide Complexes." Tetrahedron Asymmetry. 6. 1833-1836 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shioiri: "Tetraphenylphosphonium Hydrogendifluoride : A New Catalyst for Silyl-mediated Aldol Reaction and the Addition of Silylacetylenes to Carbonyl Compounds" Synlett. 1033-1034 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Suzuki: "Total Synthesis of (+/-) Furaquinocin D." J.Am.Chem.Soc.117. 10757-10758 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Tamao: "Silyl Anions" Adv.Organomet.Chem.38. 1-58 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Nakai: "Asymmetric Catalysis by a New Type of Chiral Binaphthol-Titanium Complex" Tetrahedron Lett.36. 1861-1864 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Yamamoto: Advances in Catalytic Processes, Volume 1. JAI Press Inc., 29-59 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Nakai: Advances in Catalytic Processes, Volume 1. JAI Press Inc., 124-149 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 柳澤 章: "Catahytic Enantioselective Protonation of Simple Endatewith Chiral Imide" Synlen. 372-374 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 林 昌彦: "Highly EHicient Preparation of Oprically Active 5-Hyaroxy-3-oxoesters by Enantioselective Reaction of Diketene with Aldehyder Promded by Novel Chiml Scriff Base-Titanlum Alkoxiae complexes" Tetrahedron : Asymmetry. 6. 1833-1836 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] A.Bohsako: "tetraphenylphosphonium Hydrogendifluoride : A New Catalyst for Srlyl-mediated Aldol Reactlon and the Addition of Silylaerytyleres to Carbonyl Compoundd" Synlen. 1033-1034 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 斎藤 武: "Total Synthesis of (±)-Furaguinocin D" Journal of the American Chemical Society. 117. 10757-10758 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 玉尾 晧平: "Silyl Anions" Adv.Organomet.Chem.38. 1-58 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 北本 大: "Asymmetric Catalysis bya New Type of Chiral Binaphthol-Titanium Complex" Tetrahedron Letters. 36. 1861-1864 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 石原 一彰: "Advances in Catalytic Processes,Volumel" JAI Press Inc., 194(32) (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 三上 幸一: "Advances in Catalytic Processes,Volumel" JAI Press Inc., 194(26) (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 石原一彰: "Lewis Acid Assisted Chiral Bronsted Acid (LBA) for Enantioselective Protonation of Silyl Enol Ethers and Ketene Bis (trialkylsilyl) Acetals" Journal of the American Chemical Society. 116. 11179-11180 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 林 昌彦: "Novel Enantioselective Reaction of Diketene with Aldehydes Promoted by Chiral Schiff Base-Titanium Alkoxide Complex" Journal of the Chemical Society,Chemical Communication. 341-342 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 塩入孝之: "Use of the Aryl Groups as the Carbonyl Synthon.Application to the Synthesis of Some Natural Products Containing Hydroxy Amino Acid Funotions" Pure & Applied Chemistry. 66. 2151-2154 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 鈴木啓介: "Total Synthesis of Aryl C-Glycoside Antibiotics" Pure & Applied Chemistry. 66. 2175-2178 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Akio Toshimitsu: "Reaction of Configuration in the Ritter-type Substitution Reaction of Chiral β-Arylthio Alcohols through the Anchimeric Assistance of the Arylthio Group" Tetrahedron. 50. 8997-9008 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 北本 大: "Asymmetric Catalysis by a New Type of Chiral Binaphthol-Titanium Complex" Tetrahedron Letters. 36(発表予定). (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] 丸岡 啓二: "Chiral Helical Lewis Acids for Asymmetric Diels-Alder Catalysts" The Journal of Organic Chemistry. 58. 2938-2939 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] 石原 一彰: "Mechanistic Studies of a CAB-Catalyzed Asymmetric Diels-Alder Reaction" Journal of the American Chemical Society. 115. 10412-10413 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] 林 昌彦: "Enantioselective Trimethylsilylcyanation of Some Aldehydes Catalyzed by Chiral Schiff Base-Titanium Alkoxide Complexes" The Journal of Organic Chemistry. 58. 1515-1522 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] 林 昌彦: "Novel Enantioselective Reaction of Diketene with Some Aldehydes Promoted by Chiral Schiff Base Titanium Alkoxide Complexes" Journal of the Chemical Society,Chemical Communications. (in press). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] 安東 章: "Chiral Quaternary Ammonium Fluoride.A New Reagent for Catalytic Asymmetric Aldol Reaction" Tetrahedron Letters. 34. 1507-1510 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Takamitsu Hosoya: "Total Synthesis of The Gilvocarcins" Journal of the American Chemical Society. (in press). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] 三上 幸一: "Control of Chelation/Nonchelation Stereoselection in Lanthanide-Catalyzed Aldol Reactions" Journal of the Chemical Society,Chemical Communication. 343-345 (1993)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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