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Development of Stereospecific Cross-Coupling Reactions Using Chiral a-Branched Organometallic Reagents

Research Project

Project/Area Number 23655082
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

OHMURA Toshimichi  京都大学, 工学研究科, 准教授 (00378803)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2012: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2011: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords結合形成 / 立体化学 / 遷移金属触媒 / 有機ホウ素化合物 / 立体特異的 / 立体反転 / 立体保持 / 合成化学 / 立体特異的反応 / 炭素ー炭素結合形成 / 不斉合成
Research Abstract

An efficient catalyst system was established for Suzuki-Miyaura coupling of branched alkylboron reagents bearing a nitrogen functional group at the a-position. Stereochemical course of the reaction was switchable by additives. The carbon-carbon bond formation took place with inversion of configuration, when the reaction was carried out with phenol. In contrast, zirconium alkoxide mediated the reaction with retention of configuration. Two enantiomers of optically active nitrogen-containing organic compounds could be synthesized effectively by this method.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (16 results)

All 2013 2012 2011 Other

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (12 results) (of which Invited: 1 results) Remarks (3 results)

  • [Journal Article] Inversion or Retention? Effects of Acidic Additives on the Stereochemical Course in Enantiospecific Suzuki-Miyaura Coupling of a-(Acetylamino)benzylboronic Esters2011

    • Author(s)
      Tomotsugu Awano, Toshimichi Ohmura, Michinori Suginome
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Issue: 51 Pages: 20738-20741

    • DOI

      10.1021/ja210025q

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 光学活性α-(アシルアミノ)アルキルボロン酸エステルの立体特異的鈴木-宮浦カップリング2013

    • Author(s)
      大村智通、三輪恭子、杉野目道紀
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさっキャンパス(滋賀県)
    • Year and Date
      2013-03-23
    • Related Report
      2012 Final Research Report
  • [Presentation] α-(アセチルアミノ)ベンジルボロン酸エステルのエナンチオ特異的鈴木-宮浦カップリングにおける立体反転・立体保持の精密制御2012

    • Author(s)
      大村智通、粟野知嗣、三輪恭子、杉野目道紀
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学吹田キヤンパス(吹田市)
    • Year and Date
      2012-09-15
    • Related Report
      2012 Final Research Report
  • [Presentation] Switchable Stereochemical Course in Stereospecific Suzuki-Miyaura Coupling of a-(Acetylamino)benzylboronic Esters2012

    • Author(s)
      Toshimichi Ohmura, Tomotsugu Awano, Kyoko Miwa, Michinori Suginome
    • Organizer
      XXV International Conference on OrganometallicChemistry
    • Place of Presentation
      リスボン(ポルトガル)
    • Year and Date
      2012-09-03
    • Related Report
      2012 Final Research Report
  • [Presentation] ホウ素反応剤を用いる遷移金属触媒反応の新展開2012

    • Author(s)
      大村智通
    • Organizer
      第45回有機金属若手の会夏の学校
    • Place of Presentation
      ホテルェバーグリーン富士(山梨県)
    • Year and Date
      2012-07-10
    • Related Report
      2012 Final Research Report
  • [Presentation] 立体特異的鈴木一宮浦カップリング2011

    • Author(s)
      大村智通
    • Organizer
      立体特異的鈴木一宮浦カップリング
    • Place of Presentation
      洞爺サンパレス(北海道)
    • Year and Date
      2011-09-23
    • Related Report
      2012 Final Research Report
  • [Presentation] Stereospecific Suzuki-Miyaura Coupling of a-(Acylamino)benzylboronic Esters with Aryl Halides2011

    • Author(s)
      Toshimichi Ohmura, Tomotsugu Awano, Michinori Suginome
    • Organizer
      IME Boron XIV
    • Place of Presentation
      ナイアガラフォールズ(カナダ)
    • Year and Date
      2011-09-13
    • Related Report
      2012 Final Research Report
  • [Presentation] Stereospecific Suzuki-Miyaura Coupling of α-(Acylamino)benzylboronic Esters with Aryl Halides2011

    • Author(s)
      Toshimichi Ohmura
    • Organizer
      IME Boron XIV
    • Place of Presentation
      Niagara Falls, Canada
    • Related Report
      2011 Research-status Report
  • [Presentation] 立体特異的鈴木ー宮浦カップリングの開発2011

    • Author(s)
      大村 智通
    • Organizer
      第2回分子活性化若手セミナー
    • Place of Presentation
      洞爺サンパレス(北海道)
    • Related Report
      2011 Research-status Report
  • [Presentation] ホウ素反応剤を用いる遷移金属触媒反応の新展開

    • Author(s)
      大村智通(代表者)
    • Organizer
      第45回有機金属若手の会 夏の学校
    • Place of Presentation
      ホテルエバーグリーン富士(山梨県)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Switchable Stereochemical Course in Stereospecific Suzuki-Miyaura Coupling of α-(Acetylamino)benzylboronic Esters

    • Author(s)
      Toshimichi Ohmura(代表者)、Tomotsugu Awano、Kyoko Miwa、Michinori Suginome
    • Organizer
      XXV International Conference on Organometallic Chemistry (ICOMC2012)
    • Place of Presentation
      リスボン(ポルトガル)
    • Related Report
      2012 Annual Research Report
  • [Presentation] α-(アセチルアミノ)ベンジルボロン酸エステルのエナンチオ特異的鈴木-宮浦カップリングにおける立体反転・立体保持の精密制御

    • Author(s)
      大村智通(代表者)、粟野知嗣、三輪恭子、杉野目道紀
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学吹田キャンパス(吹田市)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 光学活性α-(アシルアミノ)アルキルボロン酸エステルの立体特異的鈴木-宮浦カップリング

    • Author(s)
      大村智通(代表者)、三輪恭子、杉野目道紀
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • Related Report
      2012 Final Research Report
  • [Remarks] 研究室ホームページ

    • URL

      http://www.sbchem.kyoto-u.ac.jp/suginome-lab/jp/

    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.sbchem.kyoto-u.ac.jp/suginome-lab/jp/

    • Related Report
      2011 Research-status Report

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Published: 2011-08-05   Modified: 2019-07-29  

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