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Development of the Continuous Microflow Reaction and Multi StepProcess

Research Project

Project/Area Number 23750099
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

UENO Masaharu  東京大学, 大学院・理学系研究科, 助教 (80361509)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2011: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Keywords合成化学 / 触媒・化学プロセス / マイクロ・ナノデバイス / 連続プロセス
Research Abstract

We have developed a silver or zinc catalyzed asymmetric allylation reactions, asymmetric Michael reactions of thiols with enones and enantioselective boron conjugate additions in water. These reactions are suitable for continuous microflow reaction. Moreover, we have developed immobilized zinc catalyst for allyration reactions, and an application to flow synthesis. After optimization of flow rates, concentration of solutions, and other conditions, an excellent yield, also with good productivity were obtained.

Report

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

    (34 results)

All 2013 2012 2011 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (24 results) Remarks (3 results)

  • [Journal Article] Allylation Reactions of Aldehydes with Allylboronates in Aqueous Media: Unique Reactivity and Selectivity Observed Only in the Presence of Water2013

    • Author(s)
      Shu Kobayashi, Toshimitsu Endo, Takumi Yoshino, Uwe Schneider, Masaharu Ueno
    • Journal Title

      Chem. Asian J.

      Volume: 8

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Copper(II)-Catalyzed Enantioselective Boron Conjugate Additions to α,β-Unsaturated Carbonyl Compounds in Water2012

    • Author(s)
      S. Kobayashi, P. Xu, T. Endo, M. Ueno, T. Kitanosono
    • Journal Title

      S, Angew. Chem. Int. Ed

      Volume: 51 Issue: 51 Pages: 12763-12766

    • DOI

      10.1002/anie.201207343

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chiral-Sc Catalyzed Asymmetric Michael Addition/Protonation of Thiols with Enones in Water2012

    • Author(s)
      Taku Kitanosono, Masaru Sakai, Masaharu Ueno, Shu Kobayashi
    • Journal Title

      Org. Biomol. Chem

      Volume: 10 Pages: 7134-7147

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Bismuth Catalysts in Aqueous Media2012

    • Author(s)
      Shu Kobayashi, Masaharu Ueno, Taku Kitanosono
    • Journal Title

      Topics in Current Chemistry

      Volume: 311 Pages: 1-18

    • DOI

      10.1007/128_2011_174

    • ISBN
      9783642272387, 9783642272394
    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Chiral-Sc Catalyzed Asymmetric Michael Addition/Protonation of Thiols with Enones in Water2012

    • Author(s)
      T. Kitanosono, M. Sakai, M. Ueno, S. Kobayashi
    • Journal Title

      Org. Biomol. Chem

      Volume: 10 Issue: 35 Pages: 7134-7147

    • DOI

      10.1039/c2ob26264a

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Zinc-Catalyzed Asymmetric α-Alkylallylation and α-Chloroallylation of Aldehydes2011

    • Author(s)
      S. Kobayashi, T. Endo, M. Ueno
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Issue: 51 Pages: 12262-12265

    • DOI

      10.1002/anie.201106433

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Chiral Sc-Catalyzed Asymmetric Michael Reactions of Thiols with Enones in Water2011

    • Author(s)
      M. Ueno, T. Kitanosono, M. Sakai, S. Kobayashi
    • Journal Title

      Org. Biomol. Chem

      Volume: 9 Issue: 10 Pages: 3619-3621

    • DOI

      10.1039/c1ob05424d

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 水酸化亜鉛固定化触媒を用いたアルデヒドのアリル化反応の開発とフロー合成への展開2013

    • Author(s)
      吉野匠・上野雅晴・小林修
    • Organizer
      日本化学会第93春季年会:講演番号4E4-03、立命館大学びわこ・くさつキャンパス
    • Place of Presentation
      滋賀
    • Year and Date
      2013-03-25
    • Related Report
      2012 Final Research Report
  • [Presentation] 水酸化亜鉛を触媒として用いた含水溶媒中でのアリル化反応:水の存在下で起こる特異な有機反応2013

    • Author(s)
      上野雅晴・遠藤俊充・吉野匠・SCHNEIDER,Uwe・小林修
    • 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)
    • Year and Date
      2013-03-25
    • Related Report
      2012 Final Research Report
  • [Presentation] アンモニア水を窒素源として用いる触媒的不斉アリル位アミノ化反応の開発2013

    • Author(s)
      遠藤俊充・上野雅晴・小林修
    • 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)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 水系溶媒中でのケイ素のα,ss-不飽和カルボニル化合物への不斉共役付加反応2013

    • Author(s)
      上野雅晴・伊達知晃・小林修
    • 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)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] キラル銅(II)触媒を用いる水系溶媒中でのホウ素の不斉共役付加反応2013

    • Author(s)
      徐鵬宇・北之園拓・遠藤俊充・上野雅晴・小林修
    • 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)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] キラル銅(II)触媒を用いる水系溶媒中でのホウ素の不斉共役付加反応2013

    • Author(s)
      徐 鵬宇・北之園 拓・遠藤俊充・上野雅晴・小林 修
    • 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)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 水系溶媒中でのケイ素のα,β-不飽和カルボニル化合物への不斉共役付加反応2013

    • Author(s)
      上野雅晴・伊達知晃・小林 修
    • 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)
    • Related Report
      2012 Annual Research Report
  • [Presentation] アンモニア水を窒素源として用いる触媒的不斉アリル位アミノ化反応の開発2013

    • Author(s)
      遠藤俊充・上野雅晴・小林 修
    • 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)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 水酸化亜鉛を触媒として用いた含水溶媒中でのアリル化反応:水の存在下で起こる特異な有機反応2013

    • Author(s)
      上野雅晴・遠藤俊充・吉野 匠・SCHNEIDER, Uwe・小林 修
    • 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)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 水酸化亜鉛固定化触媒を用いたアルデヒドのアリル化反応の開発とフロー合成への展開2013

    • Author(s)
      吉野 匠・上野雅晴・小林 修
    • 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)
    • Related Report
      2012 Annual Research Report
  • [Presentation] キラルスカンジウム触媒を用いる水中におけるチオールの不斉マイケル付加反応および不斉プロトン化反応2012

    • Author(s)
      酒井克・北之園拓・上野雅晴・小林修
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉・矢上キャンパス(神奈川)
    • Year and Date
      2012-03-28
    • Related Report
      2012 Final Research Report
  • [Presentation] 集約型触媒を用いた水中に於ける直截的不斉ヒドロキシメチル化反応の開発2012

    • Author(s)
      北之園拓・上野雅晴・小林修多機能
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉・矢上キャンパス(神奈川)
    • Year and Date
      2012-03-28
    • Related Report
      2012 Final Research Report
  • [Presentation] 酸化銀(I)を触媒 とするアリルケイ素を用いる水中での アルデヒドのアリル化反応2012

    • Author(s)
      上野雅晴 ・小林修
    • Organizer
      日本化学 会第 92 春季年会
    • Place of Presentation
      慶應義塾大学日吉・矢上キャンパス(神asymmetric Michael reactions of thiols奈川)
    • Year and Date
      2012-03-27
    • Related Report
      2012 Final Research Report
  • [Presentation] アリルホウ素を用いるアルデヒドのアリル化反応における溶媒効果2012

    • Author(s)
      吉野匠・遠藤俊充・上野雅晴・小林修
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉・矢上キャンパス(神奈川)
    • Year and Date
      2012-03-27
    • Related Report
      2012 Final Research Report
  • [Presentation] 水酸化亜鉛を触媒とする水系溶媒中でのアルデヒドのα-選択的アリル化反応の開発2012

    • Author(s)
      遠藤俊充・上野雅晴・小林修
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉・矢上キャンパス(神奈川)
    • Year and Date
      2012-03-27
    • Related Report
      2012 Final Research Report
  • [Presentation] 水酸化亜鉛を触媒とする水系溶媒中でのアルデヒドのα-選択的アリル化反応の開発2012

    • Author(s)
      遠藤俊充・上野雅晴・小林 修
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉・矢上キャンパス(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] アリルホウ素を用いるアルデヒドのアリル化反応における溶媒効果2012

    • Author(s)
      吉野 匠・遠藤俊充・上野雅晴・小林 修
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉・矢上キャンパス(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] 酸化銀(I)を触媒とするアリルケイ素を用いる水中でのアルデヒドのアリル化反応2012

    • Author(s)
      上野雅晴・小林 修
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉・矢上キャンパス(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] 多機能集約型触媒を用いた水中に於ける直截的不斉ヒドロキシメチル化反応の開発2012

    • Author(s)
      北之園拓・上野雅晴・小林 修
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉・矢上キャンパス(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] キラルスカンジウム触媒を用いる水中におけるチオールの不斉マイケル付加反応および不斉プロトン化反応2012

    • Author(s)
      酒井 克・北之園拓・上野雅晴・小林 修
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉・矢上キャンパス(神奈川)
    • Related Report
      2011 Research-status Report
  • [Presentation] Asymmetric α-Selective Allylaton of Aldehydes Catalyzed by Chirel Zinc-Bipyridine Complexes in Aqueous Media2011

    • Author(s)
      Toshimitsu Endo, Masaharu Ueno, Sh uKobayashi
    • Organizer
      The 3rd Asia-OceaniaConference on Green and Sustainable Chemistry (AOC-3).
    • Place of Presentation
      Melbourne, Australia(Tuesday 6December 2011: abs#234)
    • Related Report
      2012 Final Research Report
  • [Presentation] Design and Development of Multifunctional Catalyst for Asymmetric Aldol Reactions in Water2011

    • Author(s)
      Taku Kitanosono, Masaharu Ueno, Sh uKobayashi
    • Organizer
      The 3rd Asia-Oceania Conference on Green and Sustainable Chemistry (AOC-3).
    • Place of Presentation
      Melbourne, Australia(Monday 5 December 2011: abs#211)
    • Related Report
      2012 Final Research Report
  • [Presentation] Asymmetric α-Selective Allylaton of Aldehydes Catalyzed by Chirel Zinc-Bipyridine Complexes in Aqueous Media2011

    • Author(s)
      Toshimitsu Endo, Masaharu Ueno, Shu Kobayashi
    • Organizer
      The 3rd Asia-Oceania Conference on Green and Sustainable Chemistry (AOC-3)
    • Place of Presentation
      オーストラリア
    • Related Report
      2011 Research-status Report
  • [Presentation] Design and Development of Multifunctional Catalyst for Asymmetric Aldol Reactions in Water2011

    • Author(s)
      Taku Kitanosono, Masaharu Ueno, Shu Kobayashi
    • Organizer
      The 3rd Asia-Oceania Conference on Green and Sustainable Chemistry (AOC-3)
    • Place of Presentation
      オーストラリア
    • Related Report
      2011 Research-status Report
  • [Remarks]

    • URL

      http://www.chem.s.u-tokyo.ac.jp/users/synorg/index_J.html

    • Related Report
      2012 Final Research Report
  • [Remarks] 東京大学大学院理学系研究科化学専攻有機合成化学研究室HP

    • URL

      http://www.chem.s.u-tokyo.ac.jp/users/synorg/index_J.html

    • Related Report
      2012 Annual Research Report
  • [Remarks] 研究室HP:

    • URL

      http://www.chem.s.u-tokyo.ac.jp/users/synorg/index_J.html

    • Related Report
      2011 Research-status Report

URL: 

Published: 2011-08-05   Modified: 2023-03-16  

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