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Stereoselective synthesis of alkenes using new Julia-type reagents

Research Project

Project/Area Number 17K05781
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionGifu University

Principal Investigator

Ando Kaori  岐阜大学, 工学部, 教授 (70211018)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsオレフィン化 / アルケン / シス、トランス / 立体選択的 / Julia-Kocienski反応 / オレフィン化反応 / Julia型試薬 / スルホン / 立体選択的合成 / アルケンの合成 / E-アルケン / 合成化学 / 共役ジエン / シス‐トランス選択性 / スルホン試薬 / ワンポット合成 / 有機化学 / 立体選択性
Outline of Final Research Achievements

Alkenes are an important group of compounds used in the synthesis of bioactive substances.Since there are two isomers of alkene, cis and trans, which have different properties depending on the isomer and are difficult to separate, it is necessary to develop a method to make cis and trans separately.In this study, new heteroaryl sulfone reagents were developed and various alkenes were synthesized by reacting them with aldehydes.As a result, we succeeded in selective synthesis of cis-1,3-dienes, trans-1,3-dienes, trans-2-substituted alkenes, cis-3-substituted alkenes, and trans-α,β-unsaturated aldehydes.

Academic Significance and Societal Importance of the Research Achievements

アルケンは生理活性物質に含まれ、医薬品などの合成中間体にもなる化合物である。アルケンには2つの異性体が存在し、それぞれ機能が異なるため、立体選択的な合成法の開発が必要である。本研究において、E-アルケン、Z,E-ジエン、E,E-ジエン、E-α,β-不飽和アルデヒド、Z-三置換アルケンの合成法の開発に成功した。これら方法は高い選択性、高収率を与えるだけでなく、反応操作が容易で、安価な原料から合成でき、医薬品などの合成に有用である。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (46 results)

All 2020 2019 2018 2017 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (35 results) (of which Int'l Joint Research: 13 results,  Invited: 6 results) Book (2 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] 大学の有機合成化学2019

    • Author(s)
      安藤香織
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 77 Issue: 10 Pages: 959-959

    • DOI

      10.5059/yukigoseikyokaishi.77.959

    • NAID

      130007724739

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2019-10-01
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Identification of a radical SAM enzyme involved in the synthesis of archaeosine2019

    • Author(s)
      Yokogawa Takashi、Nomura Yuichiro、Yasuda Akihiro、Ogino Hiromi、Hiura Keita、Nakada Saori、Oka Natsuhisa、Ando Kaori、Kawamura Takuya、Hirata Akira、Hori Hiroyuki、Ohno Satoshi
    • Journal Title

      Nature Chemical Biology

      Volume: 15 Issue: 12 Pages: 1148-1155

    • DOI

      10.1038/s41589-019-0390-7

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A theoretical study on the elimination reaction of acrylonitrile from 2'-O-cyanoethylated nucleosides by Bu4NF2019

    • Author(s)
      K Ando, H Saneyoshi, K Seio, M Sekine
    • Journal Title

      Tetrahedron

      Volume: 75 Issue: 1 Pages: 1-9

    • DOI

      10.1016/j.tet.2018.11.042

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 1-Methyl-1H-tetrazol-5-yl (MT) sulfones in the Julia-Kocienski olefination: Comparison with the PT and the TBT sulfones2019

    • Author(s)
      Ando, Kaori; Kawano, Daiki; Takama, Daiki; Semii, Yutaka
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 24 Pages: 1566-1569

    • DOI

      10.1016/j.tetlet.2019.05.007

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One pot preparation of Julia-Kocienski sulfides and sulfones from alcohols2019

    • Author(s)
      Ando, Kaori; Hattori, Junichiro
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 36 Pages: 151017-151017

    • DOI

      10.1016/j.tetlet.2019.151017

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of 1-Thio-a-D-Ribofuranosides Using Ribofuranosyl Iodides as Glycosyl Donors2018

    • Author(s)
      Natsuhisa Oka, Ayumi Mori, Kaori Ando
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2018 Issue: 45 Pages: 6355-6362

    • DOI

      10.1002/ejoc.201801201

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Methyl-1H-tetrazol-5-yl (MT) Sulfones in the Julia-Kocienski Olefination: Comparison with the PT and the BTB Sulfones2018

    • Author(s)
      Kaori Ando, Daiki Kawano, Daiki Takama, Yutaka Semii
    • Journal Title

      Tetrahedron Letters

      Volume: 60

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] ストレプトマイセス属細菌由来α-リボフラノシドの合成研究2020

    • Author(s)
      十市優斗、岡夏央、神藤優花、安藤香織
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] アルケンの合成:どのように立体を制御するか2019

    • Author(s)
      安藤香織
    • Organizer
      白鳳セミナー
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] One-pot Preparation of a,b-Unsaturated Aldehydes by Julia-Kocienski Reaction and Hydrolysis2019

    • Author(s)
      Haruka Watanabe, Zhu Xiaoxian, Kaori Ando
    • Organizer
      4th International Symposium on Process Chemistry, Kyoto
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] One-pot Preparation of Julia-Kocienski Sulfides and Sulfones from Alcohols2019

    • Author(s)
      Kaori Ando, Junichiro Hattori
    • Organizer
      4th International Symposium on Process Chemistry, Kyoto
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of 7-Deazaguanosie Derivatives via Glycosylation2019

    • Author(s)
      Koki Nakano, Natsuhisa Oka, Akane Fukuta, Ayumi Mori, Kaori Ando
    • Organizer
      4th International Symposium on Process Chemistry, Kyoto
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Stereoselective Synthesis of Furanosyl Sulfones and Their Application to Julia-Kocienski Reaction2019

    • Author(s)
      Kanna Suzuki, Natsuhisa Oka, Ayumi Mori, Kaori Ando
    • Organizer
      4th International Symposium on Process Chemistry, Kyoto
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] One-Step Synthesis of Cyclopentene Derivatives from Julia-Kocienski Reagents Derived from Nucleosides2019

    • Author(s)
      Minami Furuzawa, Natsuhisa Oka, Mayuka Kanda, Kaori Ando
    • Organizer
      4th International Symposium on Process Chemistry, Kyoto
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Julia-Kocienski反応を用いるハロアルケンの合成2019

    • Author(s)
      大山育巳、國居貴樹、安藤香織
    • Organizer
      令和元年度有機合成化学北陸セミナー、金沢
    • Related Report
      2019 Annual Research Report
  • [Presentation] ブロム化HWE試薬を用いる(E)-α-ブロモ-α,β-不飽和エステルの立体選択的合成2019

    • Author(s)
      井戸田美紀、安藤香織
    • Organizer
      令和元年度有機合成化学北陸セミナー、金沢
    • Related Report
      2019 Annual Research Report
  • [Presentation] 1-メチルベンゾイミダゾリルスルホンを用いるZ-1,3-ジエンの立体選択的合成2019

    • Author(s)
      浅野晴香、小林峻久、安藤香織
    • Organizer
      令和元年度有機合成化学北陸セミナー、金沢
    • Related Report
      2019 Annual Research Report
  • [Presentation] リボフラノシルスルホンの立体選択的合成法の開発とJulia-Kocienski反応への応用2019

    • Author(s)
      森歩美、岡夏、安藤香織
    • Organizer
      令和元年度有機合成化学北陸セミナー、金沢
    • Related Report
      2019 Annual Research Report
  • [Presentation] キサントシンの2位カルボニル基のリン酸化反応の開発2019

    • Author(s)
      平林洋紀、岡夏央、安藤香織
    • Organizer
      令和元年度有機合成化学北陸セミナー、金沢
    • Related Report
      2019 Annual Research Report
  • [Presentation] ヌクレオシドから誘導されるJulia-Kocienski試薬の合成と応用2019

    • Author(s)
      神田万友香、岡夏央、古沢実南、安藤香織
    • Organizer
      令和元年度有機合成化学北陸セミナー、金沢
    • Related Report
      2019 Annual Research Report
  • [Presentation] Stereoselective Synthesis of Alkenes Using Silicon and Sulfone Chemistry2018

    • Author(s)
      Kaori Ando
    • Organizer
      2018 Gordon Research Conference on Organic Reactions and Processes
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] アルケンの立体化学を制御する:PとSiとSの化学2018

    • Author(s)
      安藤香織
    • Organizer
      「化学最前線2018」
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] Stereoselective Synthesis of Z-1,3-Dienes Using 1-Methylbenzimidazolyl Sulfones2018

    • Author(s)
      Haruka Asano, Takahisa Kobayashi, and Kaori Ando
    • Organizer
      International Symposium on Main Group Chemistry Directed Towards Organic Synthesis (MACOS)、京都
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Improved Preparation of Our Methylenation Reagent 3 and Its Reaction with Ketones and Aldehydes2018

    • Author(s)
      Mai Oguchi and Kaori Ando
    • Organizer
      International Symposium on Main Group Chemistry Directed Towards Organic Synthesis (MACOS)、京都
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Z-Selective Synthesis of Trisubstituted Alkenes by the Reaction of Ketones with the Julia-Kocienski-Type Reagents2018

    • Author(s)
      Daiki Takama and Kaori Ando
    • Organizer
      International Symposium on Main Group Chemistry Directed Towards Organic Synthesis (MACOS)、京都
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Stereoselective Synthesis of Ribofuranosyl Sulfones and Their Application to Julia-Kocienski Reaction2018

    • Author(s)
      Ayumi Mori, Natsuhisa Oka, Kaori Ando
    • Organizer
      International Symposium on Main Group Chemistry Directed Towards Organic Synthesis (MACOS)、京都
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] ケトンから三置換アルケンの立体選択的合成2018

    • Author(s)
      高間大輝、安藤香織
    • Organizer
      第49回中部化学関係学協会支部連合秋季大会
    • Related Report
      2018 Research-status Report
  • [Presentation] Stereoselective Synthesis of Alkenes Using Silicon and Sulfone Chemistry2018

    • Author(s)
      Kaori Ando
    • Organizer
      2018 Organic Reactions and Processes Gordon Research Conference (ORP GRC), at Stonehill College, USA
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Stereoselective Synthesis of cis-α,β-Unsaturated Sulfones, Sulfonates, and Sulfonamides Using New Peterson Reagents2017

    • Author(s)
      Kaori Ando
    • Organizer
      International Symposium on Pure & Applied Chemistry 2017, Ho Chi Minh City, Vietnam
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Stereocontrolled synthesis of alkenes2017

    • Author(s)
      Kaori Ando
    • Organizer
      International Symposium at University Kabangsaan Malaysia
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Julia型新メチレン化試薬の合成法と反応法の改良2017

    • Author(s)
      大口真衣、安藤香織
    • Organizer
      日本プロセス化学会2017サマーシンポジウム、大阪
    • Related Report
      2017 Research-status Report
  • [Presentation] Julia反応を用いる三置換アルケンの立体選択的合成法の開発2017

    • Author(s)
      高間大輝、安藤香織
    • Organizer
      日本プロセス化学会2017サマーシンポジウム、大阪
    • Related Report
      2017 Research-status Report
  • [Presentation] キラル酸活性化剤を用いるジヌクレオシドホスホロチオエートの立体選択的合成2017

    • Author(s)
      鈴木康佑、岡夏央、安藤香織
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会、岐阜
    • Related Report
      2017 Research-status Report
  • [Presentation] HWE反応を用いたE-α,β-不飽和-α-アミノエステルの合成2017

    • Author(s)
      古田晃基、安藤香織
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会、岐阜
    • Related Report
      2017 Research-status Report
  • [Presentation] キレーション制御Peterson反応によるZ-α,β-不飽和スルホネートの合成とその応用2017

    • Author(s)
      高田麻衣、藤本健介、安藤香織
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会、岐阜
    • Related Report
      2017 Research-status Report
  • [Presentation] Julia-Kocienski型アリルスルホン試薬を用いる1,3-ジエンの立体選択的合成2017

    • Author(s)
      杉山貴明、安藤香織
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会、岐阜
    • Related Report
      2017 Research-status Report
  • [Presentation] ケトンのJulia反応による三置換アルケンの立体選択的合成2017

    • Author(s)
      高間大輝、安藤香織
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会、岐阜
    • Related Report
      2017 Research-status Report
  • [Presentation] 不斉ヨードラクトン化を経由するホモクエン酸ラクトンの合成研究2017

    • Author(s)
      見須亮太、岡夏央、孕石英義、安藤香織
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会、岐阜
    • Related Report
      2017 Research-status Report
  • [Presentation] ストレプトマイセス属細菌由来α-リボフラノシドの合成研究2017

    • Author(s)
      神藤優花、岡夏央、安藤香織
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会、岐阜
    • Related Report
      2017 Research-status Report
  • [Presentation] Julia型アルキルスルホン試薬とα,β-不飽和アルデヒドの反応によるE-1,3-ジエンの立体選択的合成2017

    • Author(s)
      武井健太、安藤香織
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会、岐阜
    • Related Report
      2017 Research-status Report
  • [Presentation] Julia-Kocienski反応とワンポット加水分解を用いるE-α,β-不飽和アルデヒドの合成2017

    • Author(s)
      朱暁賢、安藤香織
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会、岐阜
    • Related Report
      2017 Research-status Report
  • [Presentation] アリルスルホンのJulia-Kocienski反応に関する研究2017

    • Author(s)
      安藤香織、小林峻久、杉山貴明
    • Organizer
      第44回有機典型元素化学討論会、東京
    • Related Report
      2017 Research-status Report
  • [Book] アルケンの合成2018

    • Author(s)
      日本化学会、安藤 香織
    • Total Pages
      128
    • Publisher
      共立出版
    • ISBN
      9784320044685
    • Related Report
      2018 Research-status Report
  • [Book] New Horizons of Process Chemistry2017

    • Author(s)
      Kaori Ando
    • Total Pages
      285
    • Publisher
      Springer, Nature Singapore Pte Ltd.
    • ISBN
      9789811034213
    • Related Report
      2017 Research-status Report
  • [Remarks] https://www1.gifu-u.ac.jp/~ando_ap/

    • Related Report
      2018 Research-status Report
  • [Patent(Industrial Property Rights)] シクロペンテン誘導体及びシクロペンテン誘導体の製造方法2019

    • Inventor(s)
      岡夏央、安藤香織
    • Industrial Property Rights Holder
      岡夏央、安藤香織
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Related Report
      2019 Annual Research Report

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Published: 2017-04-28   Modified: 2021-02-19  

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