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Asymmetric Synthesis of Chiral Molecules

Research Project

Project/Area Number 05234103
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Research InstitutionOkayama University of Science (1994-1996)
Hokkaido University (1993)

Principal Investigator

YONEMITSU Osamu  Okayama University of Science, Faculty of Science, Professor, 理学部, 教授 (60001038)

Co-Investigator(Kenkyū-buntansha) ICHIHARA Akitami  Hokkaido University, Faculty of Agriculture, Professor, 農学部, 教授 (20000820)
HASHIMOTO Shun-ichi  Hokkaido University, Faculty of Pharmaceutical Science, Professor, 薬学部, 教授 (80107391)
HAYASHI Tamio  Kyoto University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (00093295)
YAMAMOTO Hisashi  Nagoya University, Graduate School of Engineering, Professor, 大学院・工学研究科, 教授 (10135311)
KOGA Kenji  University of Tokyo, Faculty of Pharmaceutical Science, Professor, 薬学部, 教授 (10012600)
Project Period (FY) 1993 – 1995
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥98,400,000 (Direct Cost: ¥98,400,000)
Fiscal Year 1996: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 1995: ¥10,800,000 (Direct Cost: ¥10,800,000)
Fiscal Year 1994: ¥9,500,000 (Direct Cost: ¥9,500,000)
Fiscal Year 1993: ¥75,100,000 (Direct Cost: ¥75,100,000)
Keywordsasymmetric space / typical metal catalyst / transition metal catalyst / catalytic asymmetric synthesis / asymmetric total synthesis / Lewis acid base / selective reaction / chiral compound / 典型的金属系触媒
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 this project "asymmetric synthesis of chiral molecules", which was executed by 62 organic chemists dividing into four research groups of asymmetric space, typical metal catalyst, transition metal catalyst and asymmetric total synthesis for three years beginning in 1993, was not only create various new asymmetric reactions by taking advantage of characteristics of typical and transition elements, but also to apply many enantio- and diastereoselective reactions to the synthesis of complex multi-chiral compounds including useful natural products.
During 1993-1995, many new asymmetric reactions related to Diels-Alder, ene, aldol, nitroaldol, Michael, alkylation, protonationa and hydrosilylation reactions were developed, and many syntheses of complex natural products were also completed. This report is a compilation of typical results achieved by all the project members, and will assist the promotion of new research of not only the project members but many other organic chemists.

Report

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

    (35 results)

All Other

All Publications (35 results)

  • [Publications] O.Yonemitsu: "Stereoselective Total Synthesis of Lysocellin,the Representative Polyether Antibiotic of the Lysocellin Family." Tetrahedron. 52. 551-564 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O.Yonemitsu: "Synthetic Studies of 18-Membered Anti-Tumor Macrolide,Tedanolide." Tetrahedron Lett.37. 385-388 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O.Yonemitsu: "Total Synthesis of 16-Membered Tetraene Macrolide Hygrolidin." Tetrahedron Lett.37. 9077-9080 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Yamamoto: "Catalytic Asymmetric Allylation of Aldehydes." J.Am.Chem.Soc.118. 4723-4724 (1996)

    • 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(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Hayashi: "Homochiral 2,2'-Bis(oxazolyl)-1,1'-binaphthyls as Ligands for Asymmetric Cyclopropanation." Tetrahedron:Asymmetry.7. 1603-1606 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O.Yonemitsu: "Stereoselective Total Synthesis of Lysocellin, the Representative Polyether Antibiotic of the Lysocellin Family." Tetrahedron. 52. 551-564 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O.Yonemitsu: "Synthetic Studies of 18-Membered Anti-Tumor Macrolide, Tedanolide." Tetrahedron Lett.37. 385-388 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O.Yonemitsu: "Total Synthesis of 16-Membered Tetraene Macrolide Hygrolidin." Tetrahedron Lett.37. 9077-9080 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Yamamoto: "Catalytic Asymmetric Allylation of Aldehydes." J.Am.Chem.Soc.118. 4723-4724 (1996)

    • Description
      「研究成果報告書概要(欧文)」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] T.Hayashi: "Homochiral 2,2'-Bis (oxazolyl) -1,1'-binaphthyls as Ligands for Asymmetric Cyclopropanation." Tetrahedron : Asymmetry.7. 1603-1606 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O.Yonemitsu: "Stereoselective Total Synthesis of Lysocellin,the Representative Polyether Antibiotic of the Lysocelein Family." Tetrahedron. 52. 551-564 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] O.Yonemitsu: "Synthetic Studies of 18-Membered Anti-Tumor Macrolide,Tedanolide." Tetrahedron Lett.37. 385-388 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] O.Yonemitsu: "Total Synthesis of 16-Membered Tetraene Macrolide Hygrolidin." Tetrahedron Lett.37. 9077-9080 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] H.Yamamoto: "Catalytic Asymmetric Allylation of Aldehydes." J.Am.Chem.Soc.118. 4723-4724 (1996)

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

    • Related Report
      1996 Annual Research Report
  • [Publications] T.Hayashi: "Homochiral 2,2′-Bis(oxazolyl)-1,1′-binaphthyls as Ligands for Asymmetric Cyclopropanation." Tetrahedron : Asymmetry.7. 1603-1606 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] O.Yonemitsu: "Stereoselective Total Synthesis of Lysocellin, the Representative Polyether Antibiotic of the Lysocellin Family. Part 2." Tetrahedron. 52. 551-564 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] K.Koga: "Approaches to Catalytic Asymmetric Formation and Reactions of Lithium Enolates." J. Synth. Ong. Chem. Jpn.53. 1021-1032 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Yamamoto: "Animony-Templated Macrolactamization of Tetramino Esters. Facile Synthesis of Macrocyclic Alkaloids, (±) -Buchnerine, (±) -Verbacine, (±) -Verbaskine, (±) -Verbascenine." J. Am. Chem. Soc.in press (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] T. Hayashi: "Catalytic Asymmetric Synthesis of Axially Chiral Biaryls by Palladium-Catalyzed Enantioposition-Selective Cross-Coupling." J. Am. Chem. Soc.117. 9101-9102 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] S. Hashimoto: "Asymmetric Creation of Quaternary Carbon Centers by Enantiotopically Selectibe Aromatic C-H Insertion Catalyzed by Chiral Dirhodium (II) Carboxylates." Tetrahedron Lett.36. 1491-1494 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] O.Yonemitsu: "Lewis Acid-Prompted Diastereoselective Radical Cyclization Using Chiral α,β-Unsaturated Esters." J.Am.Chem.Soc.116. 6455-6456 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] "Synthetic Studies of Halichondrin B, a Antitumor Polyether Macrolide Isolated from a Marine Sponge. 4. Synthesis of the C37-C54 Subunit via Stereoselective Construction of Three Consecutive J,K, and L Rings." Synlett. 46-48 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Koga: "Catalytic Asymmetric Benzylation of Achiral Lithium Enolates Using a Chiral Ligand for Lithium in the Presence of an Achiral Ligand." J.Am.Chem.Soc.116. 8829 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] "Asymmetric 1,2-Addition of Organolithiums to Aldimines Catalyzed by Chiral Ligand." Tetrahedron. 50. 4429 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Yamamoto: "Brφnsted acid assistedchiral Lewis acid(BLA) catalyst for asymmetric Diels-Alder reaction." J.Am.Chem.Soc.116. 1561 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] T.Hayasi: "Catalytic Asymmetric Reaction of Allylic Esters with Formic Acid Catalyzed by Palladium-MOP Complexes." J.Am.Chem.Soc.116. 775 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Nishida, A.: "New Methods for the Preparation of Optically Active Carbocycles: Asymmetric Acetalization and Lewis Acid Promoted Diastereoselective Radical Cyclization." J. Org. Chem.58. 5870-5872 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Hashimoto, S.: "Enhancement of Enantioselectivity in Intramolecular C-H Insertion Reactions of α-Diazo β-Keto Esters Catalyzed by Chiral Dirhodium(II)Carboxylates." Tetrahedron Lett.34. 5109-5112 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Hayashi, T.: "Catalytic Asymmetric Reduction of Allylic Esters with Formic Acid Catalyzed by Palladium-MOP Complexes." J. Am. Chem. Soc.116. 775-776 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Uozumi, Y.: "Catalytic Asymmetric Construction of Morpholines and Piperazines by Palladium-Catalyzed Tandem Allylic Substitution Reactions." J. Org. Chem.58. 6826-6832 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Horita, K.: "Synthetic Studies of Halichondrin B, a Antitumor Polyether Macrolide Isolated from a Marine Sponge. 3. Synthesis of the C27-C36 Subunit via Completely Stereoselective C-Glycosylation to the F Ring." Synlett. 43-45 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Horita, K.: "Synthetic Studies of Halichondrin B, a Antitumor Polyether Macrolide Isolated from a Marine Sponge. 4. Synthesis of the C37-C54 Subunit via Stereoselective Construction of Three Consecutive J,K,and L Rings." Synlett. 46-48 (1994)

    • Related Report
      1993 Annual Research Report

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

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