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2001 Fiscal Year Final Research Report Summary

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
Keywordsstereocontrol / chiral recognition / asymmetric catalysis / Asymmetric allylation / endo-Cyclization / Vinylsilane / organic synthesis / chirality
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

  • Research Products

    (22 results)

All Other

All Publications (22 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 2003-09-17  

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