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STEREOSELECTIVE SYNTHESIS OF NEW CHIRAL COMPOUNDS FROM <-AMINO ACIDS

Research Project

Project/Area Number 16550097
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionTottori University

Principal Investigator

KISE Naoki  TOTTORI UNIVERSITY, FACULTY OF ENGINNERING, PROFESSOR, 工学部, 教授 (90177824)

Project Period (FY) 2004 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,800,000 (Direct Cost: ¥3,800,000)
Fiscal Year 2006: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2005: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2004: ¥1,900,000 (Direct Cost: ¥1,900,000)
KeywordsREDUCTIVE COUPLING / IMINO ESTERS / α-AMINOACIDS / L-ASPARTIC ACID / L-GLUTAMIC ACID / AZETIDINES / β-AMINOALCOHOLS / 1,2-DIAMINES / イミノペプチド
Research Abstract

1) Electroreductive intramoleculer coupling of aromatic dimethyl imino-a,ω- esters prepared from L-aspartic acid gave chiral azetidines and pyrrolidines, while electroreduction of the corresponding a-amides afforded only chiral pyrrolidines.
2) Electroreductive intramoleculer coupling of aromatic dimethyl imino-a,ω- esters prepared from L-glutamic acid gave chiral azetidines stereo specifically. On the contrary, electroreduction of the corresponding a-amides afforded chiral piperidines.
3) Electroreductive intermolecular coupling of aromatic imines prepared from L-amino acids with acetone gave chiral amionalcohols stereoselectively.
4) Reductive homo-coupling of aromatic iminopeptides prepared from L-amino acids with zinc gave chiral 1,2-diamines stereoselectively.

Report

(4 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • 2004 Annual Research Report
  • Research Products

    (3 results)

All 2006

All Journal Article (3 results)

  • [Journal Article] Electroreductive Intramolecular Coupling of Aromatic Imino Esters : Four-membered Cyclization is Much More Favorable Than Six-membered Cyclization?2006

    • Author(s)
      木瀬直樹, 平野裕貴, 田中 義
    • Journal Title

      Organic Letters Vol.8・No.7

      Pages: 1487-1490

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Electroreductive Intramolecular Coupling of Aromatic Imino Esters : Four-membered Cyclization is Much More Favorable Than Six-membered Cyclization?2006

    • Author(s)
      Naoki Kise, yuuki Hirano, Yoshi Tanaka
    • Journal Title

      Organic Letters Vol.8, No.7

      Pages: 1487-1490

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Electroreductive Intramolecular Coupling of Aromatic Imino Esters : Four-membered Cyclization is Much More Favorable Than Six-membered Cyclization?2006

    • Author(s)
      木瀬直樹, 平野裕貴, 田中義
    • Journal Title

      Organic Letters Vol.8・No.7

      Pages: 1487-1490

    • Related Report
      2005 Annual Research Report

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Published: 2004-04-01   Modified: 2016-04-21  

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