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有機ロジウム中間体の不飽和結合への付加を起点とする新規触媒的不斉合成反応の開発

Research Project

Project/Area Number 04J01183
Research Category

Grant-in-Aid for JSPS Fellows

Allocation TypeSingle-year Grants
Section国内
Research Field Organic chemistry
Research InstitutionKyoto University
Research Fellow 徳永 礼仁  京都大学, 大学院理学研究科, 特別研究員(DC1)
Project Period (FY) 2004 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥2,800,000 (Direct Cost: ¥2,800,000)
Fiscal Year 2006: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2005: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2004: ¥1,000,000 (Direct Cost: ¥1,000,000)
Keywords触媒的不斉合成反応 / ロジウム / 不斉共役付加反応 / アリール亜鉛試薬 / アリールホウ素試薬 / アリールボロン酸 / 不斉ジエン配位子 / 不斉有機触媒 / 有機チタン試薬 / アリールイミン / 不斉アリール化反応
Research Abstract

ロジウム-binap錯体触媒を用いたクロロトリメチルシラン存在下におけるアリール亜鉛試薬の3-アリールプロペナールへの高エナンチオ選択的1,4-付加反応を見出した.この反応は,98%ee以上という非常に高いエナンチオ選択性にて進行する.また本反応により,種々の薬理活性化合物の構造中に見られる2つの異なるアリール基によって構成された不斉炭素中心を構築することができる.[Tetrahedron : Asymmetry,2006,17,607.]
ロジウム-キラルジエン錯体触媒による有機ボロン酸のキノンモノケタール類への不斉1,4-付加反応の開発に成功した.光学活性ジエン配位子として(R, R)-Ph-bod*を用いることにより,高収率かつ高エナンチオ選択性を実現することができた.この反応で得られる生成物は,従来その合成法が困難とされているカルボニル基のα位がアリール基によって置換された3級不斉炭素中心をもつ化合物へと変換することができた.[Adv.Synth.Catal. 2007,349,513.]

Report

(3 results)
  • 2006 Annual Research Report
  • 2005 Annual Research Report
  • 2004 Annual Research Report

Research Products

(12 results)

All 2007 2006 2005 2004

All Journal Article (12 results)

  • [Journal Article] Asymmetric 1,4-Addition of Organoboron Reagents to Quinone Monoketals Catalyzed by a Chiral Diene/Rhodium Complex : A New Synthetic Route to Enantioenriched 2-Aryltetralones2007

    • Author(s)
      徳永 礼仁
    • Journal Title

      Advanced Synthesis & Catalysis 349巻・4-5号

      Pages: 513-513

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Highly Enantioselective 1,4-Addition of Arylzinc Reagents to 3-Arylpropenals Catalyzed by a Rhodium-Binap Complex in the Presence of Chlorotrimethylsilane2006

    • Author(s)
      徳永 礼仁
    • Journal Title

      Tetrahedron : Asymmetry 17巻・4号

      Pages: 607-607

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Rhodium-Catalyzed Asymmetric 1,6-Addition of Arylzinc Reagents to Dienones2005

    • Author(s)
      林 民生
    • Journal Title

      Angewante Chemie International Edition 44巻・27号

      Pages: 4244-4244

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Coumarines : Asymmetric Synthesis of (R)-Tolterodine2005

    • Author(s)
      陳 剛
    • Journal Title

      Organic Letters 7巻・11号

      Pages: 2285-2285

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Aldehydes Catalyzed by a Chiral Diene-Rhodium Complex2005

    • Author(s)
      林 民生
    • Journal Title

      Chemistry Letters 34巻・11号

      Pages: 1480-1480

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Enantioselective Thiourea-Catalyzed Acyl-Mannich Reactions of Isoquinolines2005

    • Author(s)
      Mark S.Taylor
    • Journal Title

      Angewante Chemie International Edition 44巻・41号

      Pages: 6700-6700

    • Related Report
      2005 Annual Research Report
  • [Journal Article] A C_2-Symmetric Bicyclo[3.3.1]nonadiene as a Chiral Ligand for Rhodium-Catalyzed Asymmetric Arylation of N-(4-Nitrobenzenesulfonamide)arylimines2005

    • Author(s)
      乙丸 裕介
    • Journal Title

      Organic Letters 7巻・2号

      Pages: 307-310

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Mechanistic Studies on the Catalytic Cycle of Rhodium-Catalyzed Asymmetric 1,4-Addition of Arytitanate Reagents to α,β-Unsaturated Ketones2004

    • Author(s)
      徳永 礼仁
    • Journal Title

      Proceedings of the National Academy of Sciences of the United States of America 101巻・15号

      Pages: 5445-5449

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Rhodium-Catalyzed Asymmetric 1,6-Addition of Aryltitanates to Enynones Giving Axially Chiral Allenes2004

    • Author(s)
      林 民生
    • Journal Title

      Organic Letters 6巻・2号

      Pages: 305-307

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A New Entry of Nucleophiles in Rhodium-Catalyzed Asymmetric 1,4-Addition Reactions : Addtion of Organozinc Reagents for the Synthesis of 2-Aryl-4-Piperidones2004

    • Author(s)
      新谷 亮
    • Journal Title

      Journal of the American Chemical Society 126巻・20号

      Pages: 6240-6241

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Asymmetric Synthesis of Diarylmethylamines by Rhodium-Catalyzed Asymmetric Addition of Aryltitanium Reagents to Imines2004

    • Author(s)
      林 民生
    • Journal Title

      Angewante Chemie, International Edition 43巻・45号

      Pages: 6125-6128

    • Related Report
      2004 Annual Research Report
  • [Journal Article] C_2-Symmetric Bicyclo[2.2.2]octadienes as Chiral Ligands : Their High Performance in Rhodium-Catalyzed Asymmetric Arylation of N-Tosylarylimines2004

    • Author(s)
      徳永 礼仁
    • Journal Title

      Journal of the American Chemical Society 126巻・42号

      Pages: 13584-13585

    • Related Report
      2004 Annual Research Report

URL: 

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

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