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Construction of Medium-Sized Ring Compounds through Molecular Folding

Research Project

Project/Area Number 23655025
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

SAWAMURA Masaya  北海道大学, 大学院・理学研究院, 教授 (40202105)

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: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2011: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords中員環 / 金触媒 / 触媒設計 / 炭素結合 / 環状化合物 / 複素環化合物 / アルキン / ホスフィン配位子
Research Abstract

A cationic gold(I) complex bearing a semihollow-shaped triethynylphosphine ligand efficiently catalyzed cyclizations of various alkynes tethered to different nucleophilic functional groups such as alcohols, sulfonamides, and silyl enol ethers due to an entropy-based rate enhancement. Trityl-based semihollow triethynylphosphines were synthesized and employed as ligands in the gold-catalyzed 8-exo-dig cyclization of acetylene-tethered silyl enol ethers to obtain eight-membered-ring carbocycles.

Report

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

    (13 results)

All 2013 2012 2011 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results) Presentation (9 results) Remarks (1 results)

  • [Journal Article] Construction of Eight-Membered Carbocycles through Gold Catalysis with Acetylene-Tethered Silyl Enol Ethers2013

    • Author(s)
      Tomohiro Iwai, Hiori Okochi, Hideto Ito, Masaya Sawamura
    • Journal Title

      Angew, Chem. Int. Ed.

      Volume: 52 Issue: 15 Pages: 4239-4242

    • DOI

      10.1002/anie.201300265

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Use of a Semihollow-Shaped Triethynylphosphane Ligand for Efficient Formation of Six- and Seven-Membered Ring Ethers through Gold(I)-Catalyzed Cyclization of Hydroxy-Tethered Propargylic Esters2013

    • Author(s)
      Hideto Ito, Ayumi Harada, Hirohisa Ohmiya, Masaya Sawamura
    • Journal Title

      Adv. Synth. Catal.

      Volume: 355 Issue: 4 Pages: 647-652

    • DOI

      10.1002/adsc.201200949

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Intramolecular Hydroamination of Alkynic Sulfonamides Catalyzed by Gold-Triethynylphosphine Complex : Construction of Azepine Frameworks by 7-Exo-dig Cyclization2011

    • Author(s)
      Hideto Ito, Tomoya Harada, Hirohisa Ohmiya, Masaya Sawamura
    • Journal Title

      Beilstein J.Org.Chem.

      Volume: 7 Pages: 951-959

    • DOI

      10.3762/bjoc.7.106

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Presentation] Construction of Medium-Sized Rings through Gold-Catalyzed Cyclizations of Acetylenic Silyl Enol Ethers: Impact of Ligand Cavity Sizes;2012

    • Author(s)
      Tomohiro Iwai, Hiori Okochi, Hideto Ito, Masaya Sawamura
    • Organizer
      GOLD 2012
    • Place of Presentation
      Keio Plaza Hotel, Tokyo
    • Related Report
      2012 Final Research Report
  • [Presentation] 半中空トリエチニルホスフィン-金触媒によるスルホンアミドのアルキンへの分子内付加反応:含窒素7員環化合物の合成2012

    • Author(s)
      原田友哉、伊藤英人、大宮寛久、岩井智弘、澤村正也
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学、横浜市
    • Related Report
      2012 Final Research Report
  • [Presentation] 異なるキャビティーサイズを有する半中空トリエチニルホスフィンの設計と合成:金触媒環化反応への応用2012

    • Author(s)
      大河内妃織、伊藤英人、岩井智弘、大宮寛久、澤村正也
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学、横浜市
    • Related Report
      2012 Final Research Report
  • [Presentation] 半中空トリエチニルホスフィン-金(I)触媒によるプロパルギルエステル類の環化反応2012

    • Author(s)
      原田安祐美、伊藤英人、大宮寛久、澤村正也
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学、横浜市
    • Related Report
      2012 Final Research Report
  • [Presentation] 配位平衡と反応空間の高度制御に基づく遷移金属錯対触媒の設計2012

    • Author(s)
      澤村正也
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学、横浜市
    • Related Report
      2012 Final Research Report
  • [Presentation] 新規半中空トリエチニルホスフィン配位子の合成と金触媒アルキン環化反応への応用;2012

    • Author(s)
      大河内妃織、伊藤英人、岩井智弘、澤村正也
    • Organizer
      化学系学協会北海道支部2012年冬季研究発表会
    • Place of Presentation
      北海道大学、札幌市
    • Related Report
      2012 Final Research Report
  • [Presentation] Construction of Medium-Sized Rings through Gold-Catalyzed Cyclizations of Acetylenic Silyl Enol Ethers: Impact of Ligand Cavity Sizes2012

    • Author(s)
      Tomohiro Iwai
    • Organizer
      The 6th International Conference on Gold Science Technology and its Applications (GOLD 2012)
    • Place of Presentation
      Keio Plaza Hotel, Tokyo
    • Related Report
      2012 Annual Research Report
  • [Presentation] 新規半中空トリエチニルホスフィン配位子の合成と金触媒アルキン環化反応への応用2012

    • Author(s)
      大河内 妃織
    • Organizer
      化学系学協会北海道支部2012年冬季研究発表会
    • Place of Presentation
      北海道大学
    • Related Report
      2011 Research-status Report
  • [Presentation] 異なるキャビティーサイズを有する半中空トリエチニルホスフィンの設計と合成:金触媒環化反応への応用2012

    • Author(s)
      大河内 妃織
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学 矢上キャンパス
    • Related Report
      2011 Research-status Report
  • [Remarks]

    • URL

      http://wwwchem.sci.hokudai.ac.jp/~orgmet/

    • Related Report
      2012 Final Research Report

URL: 

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

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