• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

光学活性オルト置換ジアセチルアニリンを用いた不斉N-アセチル化反応の開発

Research Project

Project/Area Number 10771260
Research Category

Grant-in-Aid for Encouragement of Young Scientists (A)

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

Principal Investigator

近藤 和弘  東邦大学, 薬学部, 助手 (90277343)

Project Period (FY) 1998 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1999: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1998: ¥1,200,000 (Direct Cost: ¥1,200,000)
Keywords不斉アシル化 / エナンチオ選択的反応 / 速度論的光学分割 / アセチル化 / ラセミ体アミン / 光学活性アニリン / イミド / スルホンアミド / アミン / ラセミ体 / 光学活性
Research Abstract

酵素によるアミンの不斉アシル化は、ラセミ体を光学活性体にする目的でしばしば用いられる。しかし、非酵素的エナンチオ選択的アシル化は全く報告されていない。
申請者らは、化学量論量の光学活性diacetylanilineを用いて2級アルキルアミンのエナンチオ選択的不斉アセチル化を検討した。その結果,最高48%の不斉収率で目的とする反応が進行することを見い出した。本例はアミンのエナンチオ選択的不斉アセチル化の最初の例である(Kondo,K.;Kurosaki,T.;Murakami,Y.Synlett1998,725.)。
さらに,高いエナンチオ選択性を獲得すべく,種々の新規不斉アシル化剤の合成を行った(Yang,J.-S.;Kondo,K.;Murakami,Y.Collect.Czech.Chem.Commun.in press.)。現在,これらアシル化剤を用いたエナンチオ選択的不斉N-アシル化を検討中である。
上記内容を検討中,新しいN-C軸不斉分子を発見し,その安定性における興味深い知見を得た(Kondo,K.;Fujita,H.;Suzuki,T.;Murakami,Y.Tetrahedron Lett.1999,40,5577.;Kondo,K.;Fujita,H.;Suzuki,T.;Murakami,Y.Enantiomer in press.)。

Report

(2 results)
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (9 results)

All Other

All Publications (9 results)

  • [Publications] Kazuhiro Kondo: "Enantioselective N-Acetylation of Racemic Secondary Alkyl Amines with Chiral 2-Acetylamino-2'-diacetylamino-1,1'-binaphthyl"Synlett. 725-726 (1998)

    • Related Report
      1999 Annual Research Report
  • [Publications] Kazuhiro Kondo: "2-Chloro-N,N-dibenzoylaniline:a Selective N-Benzoylating Reagent"Chemical&Pharmaceutical Bulletin. 46・8. 1217-1219 (1998)

    • Related Report
      1999 Annual Research Report
  • [Publications] Kazuhiro Kondo: "A versatile synthon for chemoselective N-acylation reagents,2-fluoro-N-mesylaniline"J.Chem.Soc.,Perkin Trans.1. 2973-2974 (1998)

    • Related Report
      1999 Annual Research Report
  • [Publications] Kazuhiro Kondo: "A New Chiral Axis Due to N(Open-chain imide)-Ar Bond:Unexpected Racemization Effect of an Acyl Group"Tetrahedron Lett. 40・30. 5577-5580 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Kazuhiro Kondo: "Axial Chirality of Ortho-Substituted N,N-Diacylanilines:Electronic Effects of Acyl Groups on Racemization"Enantiomer. (印刷中). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Yang,Jing-Song: "Synthesis and Resolution of a New C_2-Symmetric Chiral Bis-aniline,trans-1,2-Bis(2-aminophenyl)cyclopentane"Collect.Czech.Chem.Commun.. (印刷中). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Kazuhiro Kondo: "Enantioseletive N-Acetylation of Racemic Secondary Alkyl Amines with Chiral 2-Acetylamino-2'-diacetylamino-1, 1'-binaphthyl" Synlett. 725-726 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kazuhiro Kondo: "2-Chloro-N, N-dibenzoylaniline : a Selective N-Benzoylating Reagent" Chemical & Pharmaceutical Bulletin. 46・8. 1217-1219 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kazuhiro Kondo: "A versatile synthon for chemoselective N-acylation reagents, 2-fluoro-N-mesylaniline" J.Chem.Soc., Perkin Trans.I. 2973-2974 (1998)

    • Related Report
      1998 Annual Research Report

URL: 

Published: 1998-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi