• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Dynamic Stereocontrol

Research Project

Project/Area Number 10208104
Research Category

Grant-in-Aid for Scientific Research on Priority Areas (B)

Allocation TypeSingle-year Grants
Research InstitutionKyushu University

Principal Investigator

KATSUKI Tsutomu  Kyushu University, Chemistry, Professor, 大学院・理学研究院, 教授 (40037271)

Co-Investigator(Kenkyū-buntansha) HIDAI Masanobu  Tokyo University of Science, Chemistry, Prof., 基礎工学部, 教授 (60011011)
NOYORI Ryoji  Nagoya University, Chemistry, Prof., 大学院・理学研究科, 教授 (50022554)
ITO Yoshihiko  Kyoto Pharmaceutical University, Chemistry, Prof., 製薬化学科, 教授 (40026018)
HOSOMI Akira  Tsukuba University, Chemistry, Prof., 化学系, 教授 (00004440)
MARUOKA Keiji  Kyoto University, Chemistry, Prof., 大学院・理学研究科, 教授 (20135304)
MORO-OKA Yoshihiko  Tokiwa University, Chemistry, Prof., コミュニティー振興学部, 教授 (70016731)
MURAHASHI Shun-ichi  Okayama University of Science, Chemistry, Prof., 工学部, 教授 (60029436)
NISHIGUCHI Ikuzo  Nagaoka University of Technology, Chemistry, Prof, 工学部, 教授 (20026347)
OKAMOTO Yoshio  Nagoya University, Chemistry, Prof., 大学院・工学研究科, 教授 (60029501)
Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥86,000,000 (Direct Cost: ¥86,000,000)
Fiscal Year 2001: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 2000: ¥28,100,000 (Direct Cost: ¥28,100,000)
Fiscal Year 1999: ¥27,900,000 (Direct Cost: ¥27,900,000)
Fiscal Year 1998: ¥28,500,000 (Direct Cost: ¥28,500,000)
Keywordsstereocontrol / chiral recognition / asymmetric catalysis / Asymmetric allylation / endo-Cyclization / Vinylsilane / organic synthesis / chirality / 二点配位 / 不斉アリル化 / エンド環化 / ビニルシラン / 光学活性カラム / サレン金属錯体 / 立体配座 / 電子移動型反応 / カルボニルイリド / 不斉識別能 / 不斉金属錯体触媒 / 立体配座制御 / ルイス酸活性種 / 不安定活性種 / 電極反応制御 / 非安定化カルボニルイリド / 不斉識別機構
Research Abstract

Research Project "Dynamic Stereocontrol" has been successfully carried out for three years from 1998 to 2000 and rewarded with acquisition of new concepts for dynamic stereocontrol and invention of new methodologies for stereocontrol of organic reactions, generation of active species such as radical and carbene, and chiral separation. Representative achievements of the project are i) stereocontrol of reactions of carbonyl compounds by using a conceptually new chiral bidentate Lewis acid catalyst, ii) Construction of asymmetric reaction site by dynamic control of the conformation of achiral catalyst, iii) exploration of new type of asymmetric catalyst activated by photo-irradiation, iv) enhancement of asymmetry inducing ability of chiral catalyst by synergistic influence of achiral ligand, v) exploitation of radical reaction in aqueous medium, vi) stereocontrol of carbocation species and introduction of new methodology for construction of cyclic compounds, vii) sequential generation of … More carbon radicals and carbanions : dynamic stereocontrol in the reaction sequence, viii) construction of chiral stationary phases (CSPs) for thin layer chromatography (TLC), ix) development of molecular machine, a light-powered chiral molecular motor.
In the present reasearch, the achievements obtained in the project were collected and evaluated by the research members including many distinguished chemists in our country. Furthermore, the results of the project were thouroughly discussed through the opened symposium. Based on the analysis of the results by these discussions and evaluation, the achievements were recognized to have greatly contributed to advancement of organic synthesis and chiral separation, especially to development of stereocontrol and molecular recognition.
From the analysis, the necessity of continuing promotion of dynamic stereocontrol which will lay a foundation for ecologically acceptable, atom-efficient and high-yielding synthetic chemistry and for production of completely optically pure materials was also recognized.
Report of the present research will be published as the research report entitled "Reseach on Dynamic Stereocontrol." Less

Report

(5 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (53 results)

All Other

All Publications (53 results)

  • [Publications] Kenya Nakata: "Asymmetric Epoxidation Using Photo Activated Ru(salen)Complex"Chemistry-A European Journal. 7・17. 3776-3782 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Makoto Hojo: "Iron-Catalyzed Regio-and Stereoselective Carbolithiation of Alkynes"Angewandte Chemie,Internatinal Edition in English. 40・3. 621-623 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Katsukiyo Miura: "Synthetic Utility of Stannyl Enolates as Radical Alkylating Agents"Organic Letters. 3・16. 2591-2594 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Takeshi Ooi: "Practical Approach to Meerwein-Ponndorf-Verley Reduction of Carbonyl Substrates with New Aluminum Catalysts"Angewandte Chemie,Internatinal Edition in English. 40・19. 3610-3612 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Toshinobu Ohno: "Mg-Promoted Regio-and Stereoselective C-Acylation of α,β-Unsaturated Carbonyl Compounds"Organic Letters. 3・22. 3439-3442 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Chiyo Yamamoto: "Direct Resolution of C76 Enantiomers by HPLC Using an Amylose-based Chiral Stationary Phase"Chemical Communications. 10. 925-926 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Tsutomu Katsuki: "Asymmetric Oxidation Reactions:Practical Approach in Chemistry"Oxford University Press. 244 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Niimi, T. Uchida, R. Irie, and T. Katsuki: "Highly Enantioselective Cyclopropanation with Co(II)-Salen Complexes : Control of cis - and trans -Selectivity by Rational Ligand-Design"Advanced Synthesis & Catalysis. 343-1. 79-88 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Nakata, T. Takeda, J. Mihara, T. Hamada, R. Irie, and T. Katsuki: "Asymmetric Epoxidation Using Photo Activated Ru(salen) Complex"Chemistry - A European Journal. 7-17. 3776-3782 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] B. Saito and T. Katsuki: "Ti(salen)-Catalyzed Enantioselective Sulfoxidation Using Hydrogen Peroxide as a Terminal Oxidant"Tetrahedron Letters. 42-23. 3873-3876 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Hojo, Y. Murakami, H. Aihara, R. Sakuragi, Y. Baba, and A. Hosomi: "Iron-Catalyzed Regio- and Stereoselective Carbolithiation of Alkynes"Angewandte Chemie International Edition in English. 40-3. 621-623 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Miura, N. Fujisawa, H. Saito, D. Wang, and A. Hosomi: "Synthetic Utility of Stannyl Enolates as Radical Alkylating Agents"Organic Letters. 3-16. 2591-2594 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Miura, T. Takahashi, H, Nishikori, and A. Hosomi: "Acid-Catalyzed Cyclization of Vinylsilanes Bearing a Hemiacetal Group"Chemistry Letters. 10. 958-959 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Sasaki, Y. Kondo, and K. Maruoka: "Bowl-Shaped Tris(2,6-diphenylbenzyl)tin Hydride as a Unique Reducing Agent for Radical and Ionic Chemistry"Angewandte Chemie International Edition in English. 40-2. 411-414 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Ooi, H. Ichikawa, and K. Maruoka: "Practical Approach to Meerwein-Ponndorf-Verley Reduction of Carbonyl Substrates with New Aluminum Catalysts"Angewandte Chemie International Edition in English. 40-19. 3610-3612 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Maruoka: "Chiral, Bidentate Ti(IV) Lewis Acid for Catalytic Asymmetric Synthesis"Pure & Applied Chemistry. 74. 123-128 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] C. Yamamoto, T. Hayashi, Y. Okamoto, S. Ohkubo, and T. Kato :: "Direct Resolution of C76 Enantiomers by HPLC Using an Amylose-based Chiral Stationary Phase"Chemical Communications. 10. 925-926 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Kubota, T. Kusano, C. Yamamoto, E. Yashima, and Y. Okamoto :: "Cellulose 3,5-Dimethylphenycarbamate Immobilized onto Silica Gel via Copolymerization with A Vinyl Monomer and Its Chiral Recognition Ability as A Chiral Stationary Phase for HPLC"Chemistry Letters. 7. 724-725 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] B. Chankvetadze, C. Yamamoto, and Y. Okamoto :: "Enantioseparation of Selected Chiral Sulfoxides Using Polysaccharide-type Chiral Stationary Phases and Polar Organic, Polar Aqueous-organic and Normal-phase Eluents"Journal Chromatography A. 922-1・2. 127-137 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Ohno, M.Sakai, Y.Ishino, T.Shibata, H.Maekawa, I.Nishiguchi: "Mg-Promoted Regio-and Stereoselective C-Acylation of α,β-Unsaturated Carbonyl Compounds"Organic Letters. 3-22. 3439-3442 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M.Kyoda, T.Yokoyama, H.Maekawa, T.Ohno, I.Nishiguchi: "Regioselective C-Acylation of Vinylphophorus Compounds through Electroreduction or Mg-promoted Reduction"Synlett. 10. 1535-1538 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y.Kita,H.Maekawa,Y.Yamasaki, I.Nishiguchi: "Highly Selective and Facile Synthesis of Dihydro- and Tetrahydropyridine Dicarboxylic Acid Derivatives using Electroreduction as a Key Step"Tetrahedron. 57-11. 2095-2102 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Kenya Nakata: "Asymmetric Epoxidation Using Photo Activated Ru(salen) Complex"Chemistry -A European Journal. 7・17. 3776-3782 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Makoto Hojo: "Iron-Catalyzed Regio-and Stereoselective Carbolithiation of Alkynes"Angewandte Chemie, Internatinal Edition in English. 40・3. 621-623 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Katsukiyo Miura: "Synthetic Utility of Stannyl Enolates as Radical Alkylating Agents"Organic Letters. 3・16. 2591-2594 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Takeshi Ooi: "Practical Approach to Meerwein-Ponndorf-Verley Reduction of Carbonyl Substrates with New Aluminum Catalysts"Angewandte Chemie. Internatinal Edition in English. 40・19. 3610-3612 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Toshinobu Ohno: "Mg-Promoted Regio-and Stereoselective C-Acylation of α,β-Unsaturated Carbonyl Compounds"Organic Letters. 3・22. 3439-3442 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Chiyo Yamamoto: "Direct Resolution of C76 Enantiomers by HPLC Using an Amylose-based Chiral Stationary Phase"Chemical Communications. ・10. 925-926 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Tsutomu Katsuki: "Asymmetric Oxidation Reactions : Practical Approach in Chemistry"Oxford University Press. 244 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Tatsuya Niimi: "Highly Enantioselective Cyclopropanation with Co(II)-Salen Complexes : Control of cisand trans-Selectivity by Rational Ligand-Design Enantioselection by (salen) Mn Catalyst"Advanced Synthesis & Catalysis. 343・1. 79-88 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] Kota Masutani: "Catalytic Asymmetric Aerobic Oxidation : Chemoselective Kinetic Resolution of sec-Alcohols"Tetrahedron Letter. 46・26. 5119-5123 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Akira Hosomi: "Acid-Catalyzed Cyclization of Vinylsilanes Bearing a Hydroxy Group : A New Method for Stereoselective Synthesis of Disubstituted Tetrahydrofurans"Journal of American Chemical Society. 122・46. 11348-11357 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Takateru Kubota: "Tris (cyclohexylcarbamate) s of Cellulose and Amylose as Potential Chiral Stationary Phases for High-Performance Liquid Chromatography and Thin-Layer Chromatography"Journal of American Chemical Society. 122・17. 4056-4059 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Yoshio Kita: "Highly Selective and Facile Synthesis of Dihydro-and Tetrahydropyridine Dicarboxylic Acid Derivatives Using Electroreduction as a Key Step"Tetrahedron Lettetrs. (印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] Takashi Ooi: "Practical Catalytic Enantioselective Synthesis of α,α-Dialkyl-α-Amino Acids by Chiral Phase-Transfer Catalysis"Journal of American Chemical Society. 122・21. 5228-5229 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Keiji Maruoka: "Asymmetric Reactions with Chiral Lewis Acid Catalysts In "Catalytic Asymmetric Synthesis (second eddition)"Wiley-VCH. 467-492 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Tsutomu Katsuki: "Asymmetric Epoxidation of Unfunctionalized Olefins and Related Reactions In "Catalytic Asymmetric Synthesis (second eddition)"Wiley-VCH. 287-325 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Takashi Hashihayata: "Comformational Analysis of Cationic (R,S)-and(R,R)-(salen)manganese Complexes Posessing Axial Chirality as a Chiral Element Based on X-ray Crystallography : An Explanation of the Effect of Apical Ligand on Enantioselection by(salen)Mn Catalyst"Tetrahedron. 55・7. 14599-14610 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Keishi Miura: "Dynamic Control of Ligand Conformation : Asymmetric Epoxidation Using Achiral(Salen)manganese(III)Complex"Synlett. 1999・6. 783-785 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Y. Kita: "Selective and Facile Electroreductive Synthesis ofDihydro- and Tetrahydropyridine Dicarboxylic Acids Derivatives"Tetrahedron Letters. 40・49. 8587-8590 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Chiyo Yamamoto: "Enantioseparation by Using Chitin Phenylcarbamates as Chiral Stationary Phases for High-Performance Liquid Chromatography"Chemistry Letters. 2000・1. 12-13 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Katsukiyo Miura: "Daisuke Itoh, and Akira Hosomi^*, Homolytic Allylation of Viny Iodides with Allylstannanes"Tetrahedron Letters. 40・50. 8841-8844 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Takashi Ooi: "Pentacoordinate Organoaluminum Chemistry : Catalytic Efficiency of Me3Al in the Epoxide Cleavage with Alkynyllithiums"Journal of American Chemical Society. 121・14. 3328-3333 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Takashi Ooi: "Cycloadditions : Hetero-Diels-Alder and Related Reactions In Comprehensive Asymmetric catalysis Vol. III"Springer. 1237-1254 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Akira Hosomi: "Silicon (IV)Reagents" in Lewis Acid Reagents : A Practical Approach (The Practical Approach in Chemistry Series)"Oxford Science Publications. 159-168 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Yoshino N.Ito: "What is the Origin of High Asymmetric Induction by Chiral(Salen)manganese(III)Complex?Design of Comformationally Fixed Complex and Its Application to Asymmetric Epoxidation of 2,2-Dimethylchromenes." Terahedron Letters. 39・. 4325-4328 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yukiko Noguchi: "Kinetic Resolution of Racemic Allenes by Using(Salen)manganese(III)Complex as a Catalyst" Synlett. 1998・. 543- (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshino Ishino: "Facile Synthesis of Silyl Enol Ethers by Mg-Promoted Coupling of Aliphatic Carbonyl Compounds with Trimethylsilyl Chloride" Tetrahedron Letters. 40・7. 1349-1352 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Klaus Lorenz: "Enantiomeric Enrichment of Stereolabile Chiral Spiro Compounds by Dy-namic HPLC on Chiral Stationary Phases" Angewante Chemic,International Edition. 37・13/14. 1922-1925 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hajime Ito: "New Method for Introduction of a Silyl Group into α,β-Unsaturated Carbonyl Compounds Using a Disilane Catalyzed by a Copper(I)Salt" Journal of American Chemical Society. 120・43. 11196-11197 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Takashi Ooi: "First Meerwein-Ponndorf-Verley Alkynylation;Nonorgnometallic Way for Carbonyl Alkyations" Journal of American Chemical Society. 120・. 10790-10791 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Tsutomu Katsuki: "Transition Metals for Organic Synthesis,Vol.2" Wiley-VCH, 261-271 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Akira Hosomi: "Silicon(IV)Reagents"in Lewis Acid Reagents:A Practical Approach(The Practical Approach in Chemistry Series)" Wiley-VCH, Vol.2(261-271) (1998)

    • Related Report
      1998 Annual Research Report

URL: 

Published: 1998-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi