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1995 Fiscal Year Final Research Report Summary

Steroselective Construction of Nitrogen Hetero-alicycles Using Palladium Catalyst and Its Application to the Synthesis of Natsural Products

Research Project

Project/Area Number 06672090
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionToyama University

Principal Investigator

HIRAI Yoshiro  Toyama University Faculty of Science, Professor, 理学部, 教授 (70111747)

Project Period (FY) 1994 – 1995
Keywordsstereoselective cyclization / trans (2,6) piperidine / cis (2,6) piperidine / palladium (II) catalyst / silver trifluoroacetate / (+) -prosopinine / (+) -pseudoconhydrine / (+) -palustrine
Research Abstract

The intramolecular cyclization of the optically active urethanes containing allylic alkohol was effected by treatment with bis (acetonitrile) palladium (II) chloride to give the trans (2,6) piperidine system as a single diastereoisomer. During these transformations, the Pd (II) species are not reduced and thus the catalyst can recycle without its reoxidation. On the other hand, cyclization of the simillar substrate containing allylic chloride using silver trifluoroacetate in the presence of sodium hydride afforded the cis (2,6) piperidine system. Cyclization of other substrates using these transition metal complexes was aoso examined and simillar results were obtained.
The cyclo-adducts obtained were proved to be useful chiral building blocks by their conversion into (+) -prosopinine, (+) -pseudoconhydrine, and the important synthetic intermediate of (+) -palustrine, respectively

  • Research Products

    (2 results)

All Other

All Publications (2 results)

  • [Publications] Yoshiro Hirai: "Construction of Chiral Piperidine via Enzymatic Resolution and Palkdiam-cotalyzed N-Alkylation" Chsmistry Letters. 21-22 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yoshiro Hirai and Mayumi Nagatsu: "Construction of Chiral 2-Functionalized Piperidine via Enzymatic Resolution and Palladium-catalyzed N-Alkylation" CEMISTRY LETTERS. 21-22 (1994)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1997-03-04  

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