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Highly stereoselective reduction using palladium catalysis and its application to nitrogen containing biologically active substances

Research Project

Project/Area Number 02650634
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionWaseda University

Principal Investigator

SHIMIZU Isao  Waseda University School of Science and Engineering Associate Professor, 理工学部, 助教授 (50134820)

Project Period (FY) 1990 – 1991
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 1991: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1990: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsPalladium Catalyst / Indolizidine Alkaloid / Alkenyl Oxirane / (-)-Nupharamine / Reduction with Formic Acid / (pi-Allyl) palladium Complex / ギ酸還元 / (-)ーヌファラミン / (-)ーセリユルニン / アルアニルオキシラン
Research Abstract

We have developed useful a synthetic method for preparation of nitrogen containing organic compounds using a palladium-catalyzed reaction as a key reaction. Thus, reaction of optically active alkenyl oxiranes and formic acid in the presence of a catalytic amount of palladium-phosphine complexes gives the optically active homoallylic alcohols, whose hydroxy group is substituted with a nitrogen atom selectively to give optically active amines. The delta-amino ketons or delta-amino esters obtained are cyclized to optically active piperidine or indolizidine compounds. Chiral synthesis (-)-nupharamine and the dendrobatid alkaloids 205A, 209B, and 235B were carried out from these compounds.

Report

(3 results)
  • 1991 Annual Research Report   Final Research Report Summary
  • 1990 Annual Research Report
  • Research Products

    (25 results)

All Other

All Publications (25 results)

  • [Publications] Isao SHIMIZU: "Facule Synthesis of α-Hydroxybutenolides and α-Keto-β-allyl-γ-butyrolactones" Chem.Lett.1349-1350 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Isao SHIMIZU: "Facile Synthesis of (-)-Serricornin by Means of Palladium-Catalyzed Hydrogenolysis of Alkenyloxiranes" Tetrahedror. 47. 2991-2998

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Kazuo Nagasawa: "Stereoselectire Synthesis of 1α-Hydroxyritamin D_3 A-Ring Synthons by Palladium-Catalyzed Cyclization" Tetrahedron hett.32. 4937-4941 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masato Oshima: "Synthesis and Properties of (π-Allyl) palladium Formates as Intermediates in Palladium-Catalyzed Reductive Cleavage of Allylic Acetates and Carbonates with Formic Acid" Organometallics. 10. 1221-1223 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Isao SHIMIZU: "Facile Allylation of 4,4,4-Trifluoroacetate by Palladium Catalysts." SynLett. (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Isao Shimizu, Toshiyuki Makuta, Masato Oshima: ""Facile Synthesis of alpha-Keto Acids and Esters by Palladium-Catalyzed Decarboxylation Reactions of Diallyl alpha-Oxalcarboxylates." Chem. Lett.1457-1460 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Isao shimizu, Naoto Matsuda, Yasuo Noguchi, Yoshiro Zako, KazuoNagasawa: ""Synthesis of Vitamin D_3 D Ring Synthons by Reductive Cleavage of Norbornan-6-one-2-carboxylates"" Tetrahedron Lett.31. 4899-4902 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Isao Shimizu, Kaoruko Hayashi, Masato Oshima: ""Short Stereoselective Synthesis of (-)-Serricornin"" Tetrahedron Lett.31. 4757-4758 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Isao shimizu, Hiroyuki yamazaki: ""Chiral synthesis of (-)-Nupharamine"" Chem. Lett.777-778 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] kazuo Nagasawa, Yoshiro Zako, Hideki Ishihara, Isao Shimizu: ""Stereoselective Synthesis of 1alpha-HydroxyvitamineD_3 A-Ring Synthons by Palladium-Catalyzed Cyclization." Tetrahedron Lett.32. 4937 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Isao Shimizu, Takashi Maruyama, Toshiyuki Makuta, Hajime Hasegawa: ""Facile Synthesis of alpha-Hydroxybutenolides and alpha-Keto-beta-allyl-gamma-butyrolactones"" Chem. Lett.1349-1350 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masato Oshima, Isao Shimizu, Akio Yamamoto, Fumiyuki Ozawa: ""Synthesis and Properties of (pi-Allyl) palladium Formates as Intermediates in Palladium-Cataalyzed Reductive Cleavage of Allylic Acetates and Carbonates with Formic Acid"" Organometallics. 10. 1221-1223 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Isao Shimizu, Kaoruko Hayashi, Nobuyuki Ide, masato Oshima: ""Facile Synthesis of (-) -Serricornin by Means of Palladium-Catalyzed Hydrogenolysis of Alkenyloxiranes"" Tetrahedron. 47. 2991-2998 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Isao Shimizu, Masashi Toyoda, Toru Terashima, Masato Oshima, and Hajime Hasegawa: ""Facil Allylation of 4, 4, 4-Trifluoroacetate by Palladium Catalysis"" SYNLETT.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Isao SHIMIZU: "Facile Synthesis of αーHydroxybutenolides and αーKetoーβーallylーγーbutyrolactones" Chem.Lett.1349-1350 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] ISAO SHIMIZU: "Facile Synthesis of (ー)ーSerricornin by Means of Palladiumーcatalyzed Hydrogenolysis of Alkenyloxiranes" Tetrahedror. 47. 2991-2998

    • Related Report
      1991 Annual Research Report
  • [Publications] Kazuo Nagasawa: "Stereoselectire Synthesis of 1αーHydroxyvitamin D_3 AーRing Synthons by PalladiumーCatalyzed Cyclization" Tetrahedron Lett.32. 4937-4941 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Masato Oshima: "Synthesis and Properties of (πーAllyl) palladium Formates as Intermediates in PalladiumーCatalyzed Reductive Cleavage of Allylic Acetates and Carbonates with Formic Acid" Organometallics. 10. 1221-1223 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] ISAO SHIMIZU: "Facile Allylation of 4,4,4ーTriflnoroacetate by Palladium Catalysis." Syn Lett. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] ISAO SHIMIZU: "Chiral Synthesis of (-)ーNupharamine" CHEMISTRY LETTERS. 777-778 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] ISAO SHIMIZU: "Synthesis of Vitamin D_3 DーRing Synthons by Reductive Cleavage of Norbornanー6ーoneー2ーcarboxylates" TETRAHEDRON LETTERS. 31. 4809-4902 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] ISAO SHIMIZU: "A Short Stereoselective Synthesis of (-)ーSerricornin" TETRAHEDRON LETTERS. 31. 4757-4758 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] ISAO SHIMIZU: "Facile Synthesis of Serricornin by means of Palladium Catalyzed Hydrogenolysis of Alkenyloxiranes" TETRAHEDRON. 47. (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] Masato Oshima: "Synthesis and Properties of πーAllylpalladium Formates as Intermediates in PalladiumーCatalyzed Reductive Cleavage of Allylie Acetates and Carbonates with Formic Acid" ORGANOMETALLICS. 10. (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] Yasuo Wakatsuki: "Novel Regioselection in Insertion of a 1.4ーDisubstitutedー1,3ーenyne into RutheniumーHydrogen Bonds" J.Chem.Soc.,Chem.Commun.261-263 (1991)

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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