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Development of catalytic direct addition reactions of unprotected aminoalkanes

Research Project

Project/Area Number 24655075
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

YAMASHITA Yasuhiro  東京大学, 理学(系)研究科(研究院), 准教授 (90334341)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2012: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsアミノアルカン / フルオレニリデン / 触媒反応 / 含窒素化合物
Research Abstract

We tried to investigate the catalytic direct carbon-carbon bond forming reactions of aminoalkanes using a fluorenylidene moiety as a catalytic activator. In 1,4-addition reaction of a glycine ester to an alpha,beta-unsaturated carbonyl compound, we confirmed that catalytic turnover of the fluorenylidene moiety to form a carbon-carbon bond occurred. This result revealed that catalytic activation of N-unprotected aminoalkanes was possible by using the fluorenylidene group. We also found that a N-fluorenylimine could work as a nucleophile in the presence of a base catalyst and that it reacted with another type of imine to accomplish a catalytic imine-imine cross coupling reaction.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (9 results)

All 2014 2013 2012 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (6 results) Remarks (1 results)

  • [Journal Article] Catalytic Mannich-type Reactions ofα-Aminoacetonitrile Using Fluorenylidene as a Protecting and Activating Group2012

    • Author(s)
      Yasuhiro Yamashita, Masatoshi Matsumoto, Yi-Jing Chen, Shu Kobayashi
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 37 Pages: 7558-7563

    • DOI

      10.1016/j.tet.2012.06.044

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Direct-Type Aldol Reactions of Fluorenylidene-Protected/Activated Glycine Esters with Aldehydes for the Synthesis ofβ-Hydroxy-α-amino Acid Derivatives2012

    • Author(s)
      Raphael Rahmani, Masatoshi Matsumoto, Yasuhiro Yamashita, Shu Kobayashi
    • Journal Title

      Chem. Asian J.

      Volume: 7 Issue: 6 Pages: 1191-1194

    • DOI

      10.1002/asia.201200081

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Development of catalytic imine-imine cross-coupling reactions2014

    • Author(s)
      松本正俊、原田真志、山下恭弘、小林修
    • Place of Presentation
      名古屋大学(愛知)
    • Related Report
      2013 Final Research Report
  • [Presentation] Development of Catalytic Imine-imine Cross-coupling Reactions2014

    • Author(s)
      松本正俊、原田真志、山下恭弘、小林修
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(愛知)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 触媒的イミン-イミン交差カップリング反応によるα,β-ジアミノエステルの不斉合成2013

    • Author(s)
      松本正俊、山下恭弘、小林修
    • Place of Presentation
      立命館大学(滋賀)
    • Related Report
      2013 Final Research Report
  • [Presentation] 触媒的イミン-イミン交差カップリング反応による1,2-ジアミン誘導体の効率的合成2013

    • Author(s)
      原田真志、松本正俊、山下恭弘、小林修
    • Place of Presentation
      立命館大学(滋賀)
    • Related Report
      2013 Final Research Report
  • [Presentation] 触媒的イミンーイミン交差カップリング反応によるα,βージアミノエステルの不斉合成2013

    • Author(s)
      松本正俊、山下恭弘、小林修
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀)
    • Related Report
      2012 Research-status Report
  • [Presentation] 触媒的イミン-イミン交差カップリング反応による1,2-ジアミン誘導体の効率的合成2013

    • Author(s)
      原田真志、松本正俊、山下恭弘、小林修
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀)
    • Related Report
      2012 Research-status Report
  • [Remarks] 研究室ホームページ

    • URL

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

    • Related Report
      2013 Final Research Report

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Published: 2013-05-31   Modified: 2019-07-29  

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