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Palladium-Catalyzed Asymmetric Cycloisomerization of Enynes with Chiral Sulfinyl Functionality

Research Project

Project/Area Number 09672153
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionTohoku Pharmaceutical University

Principal Investigator

HIROI Kunio  Faculty of Pharmaceutical Sciences Pharmaceutical Department Professor, 薬学部, 教授 (00012641)

Co-Investigator(Kenkyū-buntansha) MIYAUCHI Satomi  Faculty of Pharmaceutical Sciences Pharmaceutical Department Assistant, 薬学部, 助手
ABE Ikuko  Faculty of Pharmaceutical Sciences Pharmaceutical Department Assistant, 薬学部, 助手
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1998: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1997: ¥1,900,000 (Direct Cost: ¥1,900,000)
Keywordscatalytic asymmetric synthesis / asymmetric cycloisomerization / palladium-catalyzed reaction / chiral sulfinyl group / cyclopentane / enantioselectivity / stereoselectivity
Research Abstract

A transition metal-catalyzed carbon-carbon bond formation reaction is one of the most advantageous method for the stereo- and enantioselective construction of cyclic compounds. In order to develop a new useful methodology for the asymmetric synthesis of five-membered compounds, we have studied palladium-catalyzed asymmetric cycloisomerization of readily available 1,6-enyes with chiral phosphine ligands or chiral sulfinyl functionality.
1. The palladium-catalyzed asymmetric cycloisomerizations of 1 , 6-enyes with chiral phosphine ligands produced optically active cyclopentane derivative with rather high enantioselectivity. The use of a chiral ferrocenyl phosphine as a ligand provided highest enantioselectivity.
2. The palladium-catalyzed reactions of l, 6-enyes bearing chiral sulfinyl groups at the appropriate sites in the olefinic parts gave cycized compounds, 1,4-dienes and 1,3-dienes with rather high enantiomeric excess. It should be noted that the stereoselectivity, production ratios of the 1,4-dienes to the 1,3-dienes, was dependent upon the steric envilonment around the sulfinyl groups. The plausible mechanis is proposed to rationalize the stereochemical results.
3. The palladium-catalyzed reactions of 1,6-enyes bearing chiral sulfinyl groups at the sites in the acetylenic parts produced exclusively 1,4-dienes with rather low e.e.. The steric results are rationalized by the formation of palladacycic intermediates.
4. Introduction of carboxyl functions into l, 6-enye substrates enhanced enantiocontrol, presum ably due to the conformational fixation of the intermediary palladacycles.

Report

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

    (67 results)

All Other

All Publications (67 results)

  • [Publications] Kunio Hiroi: "Studies on Chiral Organosulfur Compounds. VI.The Use of a Chiral Diene Beating an Optically Active Sulfinylmethyl Group in the Lewis Acid-Catalyzed Inramolecular Asymmetric Hetero Diels-Alder Reaction" Chem.Pharm.Bull.45巻. 759-764 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi: "Asymmetric Induction Reactions. VII.Palladium-Catalyzed Asymmetric α-Allylations of Carbonyl Compounds Using Chiral Sulfonamides as Chiral Ligands." Chem.Pharm.Bull.45巻. 769-777 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi: "Chiral β-Amino Sulfoxides as Chiral Ligands in Palladium-Catalyzed Asymmetric Allylations" Heterocycles. 46巻. 77-81 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 広井 邦雄: "有機硫黄官能基を有する不斉配位子の開発とそれを用いた触媒的不斉合成" 東北薬科大学研究年報. 44巻. 1-24 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 広井 邦雄: "パラジウム触媒によるアレン化合物への求核置換反応-生成物の幾何異性に及ぼす溶媒効果-" 東北薬科大学研究年報. 44巻. 115-120 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 広井 邦雄: "キラルスルフィニル配位子を用いたニッケル触媒による不斉1,4-共役付加反応" 東北薬科大学研究年報. 44巻. 121-126 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 広井 邦雄: "1,3-Diphenyl-π-allylnickel錯体を用いたキラルEnamineの不斉アリル化反応" 東北薬科大学研究年報. 44巻. 127-134 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 広井 邦雄: "Witting縮合反応を用いた(4-置換-1, 3-butadienyl)cyclopropane類の合成研究" 東北薬科大学研究年報. 44巻. 135-142 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi: "Asymmetric Direct α, β-Functionalization of Allenes via Asymmetric Carbopalladation" Chem.Lett.397-398 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi: "Stereochemistry of Palladium-catalyzed Asymmetric Transformation of Chiral 2-Alkynyl Sulfinates into Sulfones" Chem.Lett.553-554 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi: "New Chiral ο-(Phosphinoamide)phenyl Sulfoxide Ligands in Palladium-catalyzed Asymmetric Allylic Alkylations" Tetrahedron Lett.39巻. 6499-6502 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi: "Chiral Sulfoxide Ligands Bearing Nitrogen Atoms as Stereocontrollable Coordinating Elements in Palladium-catalyzed Asymmetric Allylic Alkylations" Tetrahedron : Asymmetry. 9巻. 3797-3817 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 広井 邦雄: "キラルπ-アリルパラジウム錯体を用いた不斉合成" 東北薬科大学研究年報. 45巻(印刷中). (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 広井 邦雄: "キラルImminophosphine およびSulfimine誘導体配位子の開発とそれを用いた触媒的不斉合成" 東北薬科大学研究年報. 45巻(印刷中). (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 広井 邦雄: "触媒的Pauson-Khand反応におけるPhosphine配位子の影響" 東北薬科大学研究年報. 45巻(印刷中). (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 広井 邦雄: "分子間および分子内ラジカル反応に果たすスルホンアミド基の立体電子的効果" 東北薬科大学研究年報. 45巻(印刷中). (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 広井 邦雄: "系内にCarboxyl基を有する1, 6-Enyne化合物のパラジウム触媒による環化異性化反応" 東北薬科大学研究年報. 45巻(印刷中). (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi: "Chiral β-Phosphino Sulfoxides as Chiral Ligands in Palladium-Catalyzed Asymmetric Allylic Nucleophilic Substitution Reactions" Tetrahedron Lett.40巻. 715-718 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi: "Stereospecificity in the Carbopalladations of Chiral Allenes followed by Intramolecular Nucleophilic Substitution Reactions" Heterocycles. 50巻. 83-87 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi: "(S)-Proline-derived Chiral Ligands Bearing Organosulfur or-Selenenyl Groups as Coordinating Elements in Palladium-Catalyzed Asymmetric Allylic Alkylations" Heterocycles. 50巻. 89-94 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi: "Organosulfur Functionality as an Alternative Enantiocontrollable Coordinating Elements in Chiral Phosphine Ligands for Palladium-Catalyzed Asymmetric Allylic Alkylations" Chem.Lett.149-150 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi: "Participation of the Chiral Sulfinyl Functionality in Palladium-Catalyzed Asymmetric Vinylcyclopropane-Cyclopentene Rearrangements" Tetrahedron Lett.40巻(印刷中). (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Masayuki Umemura, Yoko Tomikawa, Masamitsu Kaneko, Fumiko Kato: "Studies on Chiral Organosulfur Compounds. VI.The Use of a Chiral Diene Bearing an Optically Active Sulfinylmethyl Group in the Lewis Acid-Catalyzed Intramolecular Asymmetric Hetero Diels-Alder Reaction." Chem.Pharm.Bull.45 (No.45). 759-764 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Takashi Hidaka, Rie Sezaki, Yumiko Imamura: "Asymmetric Induction Reactions.VII.Palladium-Catalyzed Asymmetric alpha-Allylations of Carbonyl Compounds Using Chiral Sulfonamides as Chiral Ligands." Chem.Pharm.Bull.45 (No.45). 769-777 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Yoshio Suzuki: "Chiral beta-Amino Sulfoxides as Chiral Ligands in Palladium-Catalyzed Asymmetric Allylations" Heterocycles. 46 (No.2). 77-81 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshio Suzuki, Kunio Hiroi: "Development of Chiral Ligands Bearing Organosulfur Groups and their Use in Catalytic Asymmetric Synthesis" Annual Report of Tohoku College of Pharmacy. 44. 1-24 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Fumiko Kato, Toshinori Mitsui, Kunio Hiroi: "Palladium-Catalyzed Nucleophilic Substitution Reaction of Allene Compounds : Solvent Effects on Geometry of the Products" Annual Report of Tohoku College of Pharmacy. 44. 115-120 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshio Suzuki, Kunio Hiroi: "Nickel-Catalyzed Asymmetric Conjugate Addition Reactions with Chiral Sulfinyl Ligands" Annual Report of Tohoku College of Pharmacy. 44. 121-126 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Taichi Endo, Fumiko Kato: "Asymmetric Allylations of Chiral Enamines via 1,3-Diphenyl-pi-allylnickel Complexes" Annual Report of Tohoku College of Pharmacy. 44. 127-134 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yasuki Yoshida, Munenori Okada, Yoko Kaneko, Kunio Hiroi: "Synthetic Studies on (4-Functionalized-1,3-butadienyl) cyclopropanes via Witig Condensation Reactions" Annual Report of Tohoku College of Pharmacy. 44. 135-141 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Fumiko Kato, Akiko Yamagata: "Asymmetric Direct alpha, beta-Functionalization of Allenes via Asymmetric Carbopalladation" Chem.Lett., 1998. (No.5). 397-398

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Fumiko Kato, Hajime Nakasato: "Stereochemistry of Palladium-catalyzed Asymmetric Transformation of Chiral 2-Alkynyl Sulfinates into Allenyl Sulfones" Chem.Lett., 1998. (No.6). 553-554

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Yoshio Suzuki: "New Chiral omicron- (Phosphinoamido) phenyl Sulfoxide Ligands in Palladium-catalyzed Asymmetric Allylic Alkylations" Tetrahedron Lett.39 (No.36). 6499-6502 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Yoshio Suzuki, Ikuko Abe, Yutaka Hasegawa, Ken-ichi Suzuki: "Chiral Sulfoxide Ligands Bearing Nitrogen Atoms as Stereocontrollable Coordinating Elements in Palladium-catalyzed Asymmetric Allylic Alkylations" Tetrahedron : Asymmetry. 9 (No.21). 3797-3817 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshio Suzuki, Yoshiaki Ogata, Satomi Miyauchi, Ikuko Abe, Kunio Hiroi: "Development of Chiral Iminophosphine-or Sulfimines-derived Ligands and their Use in Catalytic Asymmetric Synthesis" Annual Report of Tohoku College of Pharmacy. 45. (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Takashi Watanabe, Kunio Hiroi: "Effects of Phosphine Ligands on Catalytic Pauson-Khand Reactions" Annual Report of Tohoku College of Pharmacy. 45. (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Mikiyo Ishii, Kunio Hiroi: "Stereoelectronic Effects of Sulfonamide Functionality in Inter-and Intramolecular Radical Reactions : Effects of Lewis Acids and Substituents on Reactivity" Annual Report of Tohoku College of Pharmacy. 45. (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Jiro Adachi, Junko Kikuchi, Kunio Hiroi: "Palladium-Catalyzed Cycloisomerizations of 1,6-Enyne Compounds Bearing Carboxyl Groups" Annual Report of Tohoku College of Pharmacy. 45. (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Yoshio Suzuki, Ryoko Kawagishi: "Chiral beta-Phosphino Sulfoxides as Chiral Ligands in Palladium-Catalyzed Asymmetric Allylic Nucleophilic Substitution Reactions" Tetrahedron Lett.40 (No.4). 715-718 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Fumiko Kato, Yuko Hiratsuka, Toshinori Mitsui, Takashi Watanabe, Kunio Hiroi: "Stereospecificity in the Carbopalladations of Chiral Allenes followed by Intramolecular Nucleophilic Substitution Reactions" Heterocycles. 50 (No.1). 83-87 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Yoshio Suzuki, Ikuko Abe: "(S) -Proline-derived Chiral Ligands Bearing Organosulfur or-Selenenyl Groups as Coordinating Elements in Palladium-Catalyzed Asymmetric Allylic Alkylations" Heterocycles. 50 (No.1). 89-94 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Yoshio Suzuki, Ikuko Abe: "Organosulfur Functionality as an Alternative Enantiocontrollable Coordinating Elements in Chiral Phosphine Ligands for Palladium-Catalyzed Asymmetric Allylic Alkylations" Chem.Lett., 1999. (No.2). 149-150

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Yasuki Yoshida, Yoko Kaneko: "Participation of the Chiral Sulfinyl Functionality in Palladium-Catalyzed Asymmetric Vinylcyclopropane-Cyclopentene Rearrangements" Tetrahedron Lett.40. (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshio Suzuki, Yoshiaki Ogata, Kunio Hiroi: "A New Chiral Iminophosphine Ligand Derived from (1S,4S) -Fenchone in Palladium-Catalyzed Asymmetric Allylic Alkylations" Tetrahedron : Asymmetry. 10. (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi, Yoshio Suzuki, Ikuko Abe: "(S) -Proline-derived New Chiral Ligands with Phosphino, Organosulfur or Organoselenenyl Functionality as an Enantiocontrollable Element" Tetrahedron : Asymmetry. 10. (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kunio Hiroi: "Asymmetric Direct α,β-Functionalization of Allenes via Asymmetric Carbopalladation" Chem.Lett.397-398 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kunio Hiroi: "Stereochemistry of Palladium-catalyzed Asymmetric Transformation of Chiral 2-Alkynyl Sulfinates into Sulfones" Chem.Lett.553-554 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kunio Hiroi: "New Chiral o-(Phosphinoamido)phenyl Sulfoxide Ligands in Palladium-catalyzed Asymmetric Allylic Alkylations" Tetrahedron Lett.39巻. 6499-6502 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kunio Hiroi: "Chiral Sulfoxide Ligands Bearing Nitrogen Atoms as Stereocontrollable Coordinating Elements in Palladium-catalyzed Asymmetric Allylic Alkylations" Tetrahedron:Asymmetry. 9巻. 3797-3817 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 広井 邦雄: "キラルπ-アリルパラジウム錯体を用いた不斉合成" 東北薬科大学研究年報. 45巻(印刷中). (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 広井 邦雄: "キラルIminophosphineおよびSulfimine誘導体配位子の開発とそれを用いた触媒的不斉合成" 東北薬科大学研究年報. 45巻(印刷中). (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 広井 邦雄: "触媒的Pauson-Khand反応におけるPhosphine配位子の影響" 東北薬科大学研究年報. 45巻(印刷中). (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 広井 邦雄: "分子間および分子内ラジカル反応に果たすスルホンアミド基の立体電子的効果" 東北薬科大学研究年報. 45巻(印刷中). (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 広井 邦雄: "系内にCarboxyl基を有する1,6-Enyne化合物のパラジウム触媒による環化" 東北薬科大学研究年報. 45巻(印刷中). (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kunio Hiroi: "Chiral β-Phosphino Sulfoxides as Chiral Ligands in Palladium-Catalyzed Asymmetric Allylic Nucleophilic Substitution Reactions" Tetrahedron Lett.40巻. 715-718 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kunio Hiroi: "Stereospecificity in the Carbopalladations of Chiral Allenes Followed by Intramolecular Nucleophilic Substitution Reactions" Heterocycles. 50巻. 83-87 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kunio Hiroi: "(S)-Proline-derived Chiral Ligands Bearing Organosulfur or -Selenenyl Groups as Coordinating Elements in Palladium-Catalyzed Asymmetric Allylic Alkylations" Heterocycles. 50巻. 89-94 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kunio Hiroi: "Organosulfur Functionality as an Alternative Enantiocontrollable Coordinating Elements in Chiral Phosphine Ligands for Palladium-Catalyzed Asymmetric Allylic Alkylations" Chem.Lett.149-150 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kunio Hiroi: "Participation of the Chiral Sulfinyl Functionality in Palladium-Catalyzed Asymmetric Vinylcyclopropane-Cyclopentene Rearrangements" Tetrahedron Lett.40巻(印刷中). (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kunio Hiroi: "Studies on Chiral Organosulfur Compounds. VI. The Use of a Chiral Diene Bearing an Optically Active Sulfinylmethyl Group in the Lewis Acid-Catalyzed Intramolecular Asymmetric Hetero Diels-Alder Reaction" Chem.Pharm.Bull.45号. 759-764 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kunio Hiroi: "Asymmetric Induction Reactions. VII. Palladium-Catalyzed Asymmetric α-Allylations of Carbonyl Compounds Using Chiral Sulfonamides as Chiral Ligands." Chem.Pharm.Bull.45号. 769-777 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kunio Hiroi: "Chiral β-Amino Sulfoxides as Chiral Ligands in Palladium-Catalyzed Asymmetric Allylations" Heterocycles. 46号. 77-81 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 広井邦雄: "有機硫黄官能基を有する不斉配位子の開発とそれを用いた触媒的不斉合成" 東北薬科大学研究年報. 44号(印刷中). (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 広井邦雄: "パラジウム触媒によるアレン化合物への求核置換反応-生成物の幾何異性に及ぼす溶媒効果-" 東北薬科大学研究年報. 44号(印刷中). (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 広井邦雄: "キラルスルフィニル配位子を用いたニッケル触媒による不斉1,4-共役付加反応" 東北薬科大学研究年報. 44号(印刷中). (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 広井邦雄: "6.1,3-Diphenyl-π-allylnickel錯体を用いたキラルEnamineの不斉アリル化反応" 東北薬科大学研究年報. 44号(印刷中). (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 広井邦雄: "Wittig縮合反応を用いた(4-置換-1,3-butadienyl)cyclopropane類の合成研究" 東北薬科大学研究年報. 44号(印刷中). (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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