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2013 Fiscal Year Final Research Report

Asymmetric Synthesis of Amino Acids from Carbon Dioxide

Research Project

  • PDF
Project/Area Number 24750081
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

MITA TSUYOSHI  北海道大学, 薬学研究科(研究院), 助教 (00548183)

Project Period (FY) 2012-04-01 – 2014-03-31
Keywordsアミノ酸 / 二酸化炭素 / 固定化 / アミノシラン / フッ化セシウム / イミン / 遷移金属錯体 / 不斉合成
Research Abstract

A catalytic enantioselective silylation of N-tert-butylsulfonylimines using a copper-secondary diamine complex was demonstrated. The resulting optically active amino silanes could be carboxylated under a CO2 atmosphere (1 atm) to afford the corresponding amino acids in a stereoretentive manner. This two-step sequence provides a new synthetic protocol for optically active amino acids from gaseous CO2 and imines in the presence of a catalytic amount of a chiral source.

  • Research Products

    (15 results)

All 2014 2013 2012 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (7 results) (of which Invited: 1 results) Remarks (1 results)

  • [Journal Article] Carboxylation with CO2 via Brook Rearrangement : Preparation ofα-Hydroxy Acid Derivatives2014

    • Author(s)
      Tsuyoshi Mita, Yuki Higuchi, Yoshihiro Sato
    • Journal Title

      Org. Lett.

      Volume: 16 Pages: 14-17

    • DOI

      10.1021/ol403099f

    • Peer Reviewed
  • [Journal Article] One-Pot ^Synthesis ofα-Amino Acids from CO_2 Using Bismetal Reagents2013

    • Author(s)
      Tsuyoshi Mita, Yoshihiro Sato
    • Journal Title

      J. Synth. Org. Chem., Jap.

      Volume: 71 Pages: 1163-1171

    • Peer Reviewed
  • [Journal Article] Iridium- and Rhodium-Catalyzed Dehydrogenative Silylations of C(sp^3)-H Bonds Adjacent to a Nitrogen Atom Using Hydrosilanes2013

    • Author(s)
      Tsuyoshi Mita, Kenichi Michigami, Yoshihiro Sato
    • Journal Title

      Chem. Asian J.

      Volume: 8 Pages: 2970-2973

    • DOI

      10.1002/asia.201300930

    • Peer Reviewed
  • [Journal Article] Iridium-Catalyzed Triple C(sp^3)-H Borylations : Construction of Triborylated sp^3-Carbon Centers2013

    • Author(s)
      Tsuyoshi Mita, Yuto Ikeda, Kenichi Michigami, Yoshihiro Sato
    • Journal Title

      Chem. Commun.

      Volume: 49 Pages: 5601-5603

    • DOI

      10.1039/c3cc42675k

    • Peer Reviewed
  • [Journal Article] One-Step Synthesis of Racemicα-Amino Acids from Aldehydes, Amine Components, and Gase ous CO_2 by the Aid of a Bismetal Reagent2013

    • Author(s)
      Tsuyoshi Mita, Yuki Higuchi, Yoshihiro Sato
    • Journal Title

      Chem. Eur. J.

      Volume: 19 Pages: 1123-1128

    • DOI

      10.1002/chem.201202332

    • Peer Reviewed
  • [Journal Article] One-Pot Synthesis of ^α-Amino Acids from CO_2 Using a Bismetal Reagent with Si-B Bond2012

    • Author(s)
      Tsuyoshi Mita, Jianyang Chen, Masumi Sugawara, Yoshihiro Sato
    • Journal Title

      Org Lett.

      Volume: 14 Pages: 6202-6205

    • DOI

      10.1021/ol302952r

    • Peer Reviewed
  • [Journal Article] Sequential Protocol for C(sp^3)-H ^Carboxylation with CO_2 : Transition Metal-Catalyzed Benzylic C-H Silylation and Fluoride-Mediated Carboxylation2012

    • Author(s)
      Tsuyoshi Mita, Kenichi Michigami, Yoshihiro Sato
    • Journal Title

      Org. Lett.

      Volume: 14 Pages: 3462-3465

    • DOI

      10.1021/ol301431d

    • Peer Reviewed
  • [Presentation] ルテニウム触媒を用いた1-アリールピラゾール類のC-H結合シリル化、続くCO2ガスによるカルボキシル化反応の開発2014

    • Author(s)
      美多剛, 田中寛之, 道上健一, 佐藤美洋
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学(熊本県)(口頭発表, 査読無, 28R-pm15)
    • Year and Date
      2014-03-28
  • [Presentation] One-Pot Synthesis ofα-Amino Acids Using CO^2 viaα-Amino Carbanion Intermediates2013

    • Author(s)
      Tsuyoshi Mita, Masumi Sugawara, Jianyang Chen, Yoshihiro Sato
    • Organizer
      ISCC-10 (10^<th> International Symposium on Carbanion Chemistry)
    • Place of Presentation
      同志社大学・寒梅館(京都府)(口頭発表, 査読有, SIL-24)
    • Year and Date
      2013-09-26
  • [Presentation] One-Pot Synthesis ofα-Amino Acids from Three Basic Materials : ^<an> Aldehyde, an Amine, and CO^22013

    • Author(s)
      Tsuyoshi Mita, Yuki Higuchi, Yoshihiro Sato
    • Organizer
      OMCOS 17 (17^<th> Organometallic Chemistry Directed Towards Organic Synthesis)
    • Place of Presentation
      Lincoln Center (Fort Collins, CO, USA)(ポスター発表, 査読有, Poster 168)
    • Year and Date
      2013-07-29
  • [Presentation] 遷移金属触媒を用いたC(sp^3)-H結合のシリル化反応の開発と二酸化炭素ガスによるアミノ酸骨格の構築2013

    • Author(s)
      美多剛, 道上健一, 池田祐人, 佐藤美洋
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜(神奈川県)(ポスター発表, 査読無, 30amA-652)
    • Year and Date
      2013-03-30
  • [Presentation] 二酸化炭素ガス、フッ化セシウム、およびSn、Si、Bを用いる有機合成 : α-アミノ酸のワンポット合成、並びに触媒的C-Hカルボキシル化の開発2012

    • Author(s)
      美多剛
    • Organizer
      若手研究者のための有機化学札幌セミナー
    • Place of Presentation
      北海道大学(北海道)(口頭発表, 査読有)
    • Year and Date
      2012-11-26
    • Invited
  • [Presentation] One-Step Synthesis ofα-Amino Acids from Aldehydes, Sulfonamides, ^and Gaseous CO2 ^Using a Bismetal Reagent2012

    • Author(s)
      Tsuyoshi Mita, Yuki Higuchi, Yoshihiro Sato
    • Organizer
      IKCOC-12 (12^<th> International Kyoto Conference on New Aspects of Organic Chemistry)
    • Place of Presentation
      リーガロイヤルホテル京都(京都府)(ポスター発表, 査読有, PC-127)
    • Year and Date
      2012-11-15
  • [Presentation] One-Pot Synthesis of alpha-Amino Acids from Imines or Aldehydes ^<Us>ing CO2 ^Gas2012

    • Author(s)
      Tsuyoshi Mita, Jianyang Chen, Masumi Sugawara, Yuki Higuchi, Yoshihiro Sato
    • Organizer
      Gordon Research Conference 2012, Organic Reactions & Processes
    • Place of Presentation
      Bryant University (Smithfield, RI, US)(口頭発表, 査読有, Poster Session II-15)
    • Year and Date
      2012-07-18
  • [Remarks] 研究室ホームページ

    • URL

      http://gouka.pharm.hokudai.ac.jp/FSC/jpn/page/top_page.htm

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Published: 2015-06-25  

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