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Development of Chiral Ligand Based on Double Asymmetric Induction and Application to Catalytic Reaction.

Research Project

Project/Area Number 08455433
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS

Principal Investigator

SUZUKI Akira  KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS,FACULTY OF SCIENCE AND INDUSTRIAL TECHNOLOGY,PROFESSOR, 産業科学技術学部, 教授 (40001185)

Co-Investigator(Kenkyū-buntansha) OKUMOTO Hiroshi  KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS,FACULTY OF SCIENCE AND INDUSTRIAL T, 産業科学技術学部, 助教授 (90183251)
Project Period (FY) 1996 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥5,600,000 (Direct Cost: ¥5,600,000)
Fiscal Year 1998: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1997: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1996: ¥2,400,000 (Direct Cost: ¥2,400,000)
KeywordsPALLADIUM CATALYST / ASYMMETRIC REACTION / CHIRAL LIGAND / 不斉誘起 / 不斉触媒反応 / 重複不斉反応 / 有機金属触媒
Research Abstract

The envisioned ligand is monodentate phosphine ligand for palladium catalyst. The new chiral ligand was designed based on the double asymmetric induction methodology which is well known in a usual asymmetric reaction. Thus, the combination of axial chirality and chiral auxiliary constitutes the backbone of the chiral ligand. Initially, the axially chiral fragment was binaphthalene framework, because the skeleton has been proved to exhibit most efficient induction ability. As an another chiral auxiliary, oxazohdine and acetal structures were selected. Diphenylphosphino group and chiral auxiliary were planned to be put on 2 and 2' positions on the binaphthalene framework. Although the most desired ligand could not be synthesized in spite of intensive trials, another ligand was prepared and tested in several palladium catalyzed reactions. Unfortunately, the high asymmetric induction was not observed so far under the typical reaction conditions in each catalyzed reaction. However, this concept is believed to be anew direction to obtain more efficient chiral ligand.

Report

(4 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • 1996 Annual Research Report
  • Research Products

    (28 results)

All Other

All Publications (28 results)

  • [Publications] 鈴木 章: "ハロボレーションとその関連反応" Crgamcmetallic News. 3. 77-95 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A. Suzuki: "Haloboration to Alkynes and the Related Reactions" Advances in Boron Chemistry. 17. 163-170 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A. Suzuki: "Haloboration of 1-Alkynes and Its Synthetic Application" Reviews on Heteroatom Chemistry. 17. 271-314 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S. Hara: "Synthesis of 4-(2-Bromo-2-propenyl)-4-methyl-" Org. Syn.75. 129-138 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S. Hara: "The Regio-selectiul 1.4-Addition Reaction of" Bull. Chem. Soc. Jpn.71. 2403-2408 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A. Suzuki: "Palladium-Catalyzed Carbonylrtive Cross-Coupling" J. Org. Chem.63. 4726-4731 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A. Suzuki: "Cross-Coupling Reaction of Orgeno bonon Compounds with orgavic Halides" Wiley-VCH, 48 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A.Suzuki: "New Synthetic Reactions Using Organoboron Derivatives in the Presence of Palladium Complexas and Bases" Proceedings of the 7th OCRC International Symposium : Organometallics Directed Towards Organic Synthesis. 1. (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Ishiyama, N.Matsuda, M.Murata, F.Ozawa, A.Suzuki, and N.Miyaura: "Platinum(0)-Catalyzed Diboration of Alkynes with Tetrakis (alkoxo) diborons : An Efficient and Convenient Approach to cis-Bis (boryl) alkenes" Organometsllics. 15. 713 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Sakai, S.Saito, G.Kanai, A.Suzuki, and N.Miyaura: "Olefination and Hydroxymethylation of Aldehydes Using Knochel's (Dialkoxybory1)-methylcopper Reagents" Tetrahedron. 52. 915 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A.Suzuki: "Haloboration, Thioboration, and Diboration Reactions" Proceedings of the 8th Japan-Korea Seminar in Organic Chemistry, Tokyo. 134 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yamamoto, S.Hara, and A.Suzuki: "Enantioselective Synthesis of Quaternary Carbon in Homoallylic Alcohols by the Reaction of Tartrate Ester Derivatives of 3,3-Disubstituted Allylborane with Aldehydes." Synlett. 883. (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Hara, S.Ishimura, and A.Suzuki: "Cyanuric Fluoride-Induced 1,4-Addition Reaction of Alkenylboronic Acids to alpha, beta-Unsaturated Ketones. Stereoselective Synthesis of gamma, delta-Unsaturated Ketones Having Functionalities." Synlett. 993. (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yamamoto, S.Hara, and A.Suzuki: "Enantioselective Synthesis of Ipsenol and Ipsdienol Using a (2-Bromoallyl) boran Derivative" Synth.Commun..27. 1029 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A.Suzuki, "Advances in Boron Chemistry": "Haloboration to Alkynes and the Related Reactions" The Royal Society of Chemistry, London. 163-170 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A.Suzuki: "Haloboration of 1-Alkynes and Its Synthetic Application" Reviews on Heteroatom Chemistry, Myu, Tokyo. 17. 271-314 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Hara and A.Suzuki: "Synthesis of 4-(2-Bromo-2-propenyl)-4-methyl-g-butyrolactone by the Reaction of Ethyl Levulinate with (2-bromoallyl) diisopropoxyborane Prepared by Haloboration of Allene" Org.Synth.75. 129-138 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A.Suzuki: "Cross-coupling Reactions of Organoboron Compounds with Organic Halides" "Metal-catalyzed Cross-coupling Reactions", Wiley-VCH,Weinheim, Germany. 49-97 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Hara, H.Shudoh, S.Ishimura, and A.Suzuki: "The Regioselective 1,4-Addition Reaction of Alkenylboronic Acids to alpha, beta, alpha', beta'-Unsaturated Ketones" Bull.Chem.Soc.Jpn.71. 2403-2408 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Ishiyama, T. ; Kizaki, H. ; Hayashi, T ; Miyaura, N. ; Suzuki, A.: "Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles : Synthesis of Biaryl Ketones." J.Org.Chem.63. 4726-4731 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 鈴木 章: "ハロボレーションとその関連反応" Organometallic News. 3. 77-95 (1996)

    • Related Report
      1998 Annual Research Report
  • [Publications] A.Suzuki: "Haloboration to Alkynes and the Related Reactions" Advances in Boron Chemistry. 17. 163-170 (1997)

    • Related Report
      1998 Annual Research Report
  • [Publications] A.Suzuki: "Haloboration of 1-Alkynes and Its Synthetic Application" Reviews on Heteroation Chemistry. 17. 271-314 (1997)

    • Related Report
      1998 Annual Research Report
  • [Publications] S.Hara: "Synthesis of 4-(2-Bromo-2-propenyl)-4-methyl-" Org.Syn.75. 129-138 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] S.Hara: "The Regio-selective 1,4-Addition Reaction of Alkenyl" Bull.Chem.Soc.Jpn. 71. 2403-2408 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] A.Suzuki: "Palladium-Catalyzed Carbonylative Cross-Coupling Reactions" J.Org.Chem. 63. 4726-4731 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] A.Suzuki: "Cross-Coupling Reactions of Organoboron Compounds with Organic Halidis in “Metal-Catalyzed Cross-coupling Reactions"" Wiley-VCH, 48 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Akira Suzuki: "Haloboration of 1-Alkylles and its Synthetic Application" Reviews on Heteroatom Chemistry. Vol17. 271-314 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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