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2012 Fiscal Year Final Research Report

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

Research Project

  • PDF
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
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
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.

  • Research Products

    (8 results)

All 2013 2012 2011 Other

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (6 results) Remarks (1 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 Pages: 20738-20741

    • DOI

      DOI:10.1021/ja210025q

    • 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [Remarks]

    • URL

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

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Published: 2014-09-25  

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