• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Development of an amine-Lewis acid co-catalytic system as multifunctional catalysts

Research Project

Project/Area Number 25708016
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypePartial Multi-year Fund
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

Kano Taichi  京都大学, 理学研究科, 准教授 (40372560)

Project Period (FY) 2013-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥26,000,000 (Direct Cost: ¥20,000,000、Indirect Cost: ¥6,000,000)
Fiscal Year 2016: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2015: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2014: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2013: ¥11,830,000 (Direct Cost: ¥9,100,000、Indirect Cost: ¥2,730,000)
Keywords有機分子触媒 / 共役付加反応 / 合成化学 / アミン有機触媒 / 共役付加
Outline of Final Research Achievements

Enolizable aldehydes can be utilized as nucleophiles by converting to enamines, and various amine-catalyzed reactions including Mannich reaction with imines have been developed to date. In the present study, carbamates such as BocNH2 was found to be applicable as a novel organocatalyst to activate aldehydes. It was found that the Mannich-type reaction between Boc-protected aminals and aldehydes proceeds in the presence of a phosphoric acid catalyst. Since less basic carbamates do not deactivate the strong Bronsted acid catalyst, carbamate-Bronsted acid cocatalyst system would be applicable to the reactions using less reactive electrophiles. The asymmetric variant of the present Mannich-type reaction through dual activation of aldehydes and aminals has also been demonstrated with a chiral phosphoric acid catalyst.

Report

(6 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • Research Products

    (22 results)

All 2018 2017 2016 2015 2014 2013

All Journal Article (13 results) (of which Peer Reviewed: 13 results,  Acknowledgement Compliant: 4 results) Presentation (9 results) (of which Int'l Joint Research: 1 results,  Invited: 2 results)

  • [Journal Article] Catalyst-controlled diastereoselectivity reversal in the formation of dihydropyrans2017

    • Author(s)
      Taichi Kano, Hiroki Maruyama, Chihiro Homma, Keiji Maruoka
    • Journal Title

      Chemical Communications

      Volume: 54 Issue: 28 Pages: 3496-3499

    • DOI

      10.1039/c8cc01443d

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of Less Accessible a-Tertiary Amines from Alkynyl Z-Ketimines2017

    • Author(s)
      Taichi Kano, Yusuke Aota, Keiji Maruoka
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 56 Issue: 51 Pages: 16293-16296

    • DOI

      10.1002/anie.201710084

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Chiral Tritylpyrrolidine Derivatives and Their Application to Asymmetric Benzoyloxylation2017

    • Author(s)
      Mio Shimogaki, Hiroki Maruyama, Shingo Tsuji, Chihiro Homma, Taichi Kano, Keiji Maruoka
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 23 Pages: 12928-12932

    • DOI

      10.1021/acs.joc.7b02562

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalyst-Controlled, Enantioselective, and Diastereodivergent Conjugate Addition of Aldehydes to Electron-Deficient Olefins2017

    • Author(s)
      S. B. Jennifer Kan, Hiroki Maruyama, Matsujiro Akakura, Taichi Kano, Keiji Maruoka
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 56 Issue: 32 Pages: 9487-9491

    • DOI

      10.1002/anie.201705546

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] In situ generation of N-Boc-protected alkenyl imines: controlling the E/Z geometry of alkenyl moieties in the Mukaiyama-Mannich reaction2017

    • Author(s)
      Bai Jian-Fei、Sasagawa Hajime、Yurino Taiga、Kano Taichi、Maruoka Keiji
    • Journal Title

      Chemical Communications

      Volume: 53 Issue: 58 Pages: 8203-8206

    • DOI

      10.1039/c7cc04674j

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] In situ generation of less accessible Boc-imines from aldehydes: construction of a quaternary carbon by the Mannich reaction or unprecedented aldol reaction2017

    • Author(s)
      Taichi Kano, Chihiro Homma, Keiji Maruoka
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 15 Issue: 21 Pages: 4527-4530

    • DOI

      10.1039/c7ob01126a

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of N‐Boc-Propargylic and Allylic Amines by Reaction of Organomagnesium Reagents with N‐Boc-Aminals and Their Oxidation to N‐Boc-Ketimines2016

    • Author(s)
      加納太一、小林遼平、丸岡啓二
    • Journal Title

      Org. Lett.

      Volume: 18 Issue: 2 Pages: 276-279

    • DOI

      10.1021/acs.orglett.5b03446

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] N-Boc-aminals as easily accessible precursors for less accessible N-Boc-imines: facile synthesis of optically active propargylamine derivatives using Mannich-type reactions2016

    • Author(s)
      Taiga Yurino, Yusuke Aota, Daisuke Asakawa, Taichi Kano, Keiji Maruoka
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 26 Pages: 3687-3700

    • DOI

      10.1016/j.tet.2016.03.076

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rate Acceleration of Solid-Liquid Phase-Transfer Catalysis by Rotor-Stator Homogenizer2016

    • Author(s)
      Taichi Kano, Yusuke Aota, Keiji Maruoka
    • Journal Title

      Advanced Synthesis and Catalysis

      Volume: 358 Issue: 18 Pages: 2996-2999

    • DOI

      10.1002/adsc.201600425

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regio- and Stereoselective Conjugate Addition of Aldehydes to β-Tosyl Enones Catalyzed by Binaphthyl-Modified Chiral Amine2015

    • Author(s)
      Taichi Kano, Hisashi Sugimoto, Hiroki Maruyama, Keiji Maruoka
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 54 Issue: 29 Pages: 8462-8465

    • DOI

      10.1002/anie.201500225

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Versatile In Situ Generated N-Boc-Imines: Application to Phase- Transfer-Catalyzed Asymmetric Mannich-Type Reactions2015

    • Author(s)
      加納太一、小林遼平、丸岡啓二
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 54 Issue: 29 Pages: 8471-8474

    • DOI

      10.1002/anie.201502215

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Brønsted Acid-catalysed Mannich Reaction Through Dual Activation of Aldehydes and N-Boc-Imines2015

    • Author(s)
      Taichi Kano, Yusuke Aota, Daisuke Asakawa, Keiji Maruoka
    • Journal Title

      Chemical Communications

      Volume: 51 Issue: 92 Pages: 16472-16474

    • DOI

      10.1039/c5cc07290e

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Metal-Free Enantioselective Hydroxyamination of Aldehydes with Nitrosocarbonyl Compounds Catalyzed by an Axially Chiral Amine2013

    • Author(s)
      T. Kano, F. Shirozu, K. Maruoka
    • Journal Title

      Journal of the American Chemical Society

      Volume: 135 Issue: 48 Pages: 18036-18039

    • DOI

      10.1021/ja4099627

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] Catalyst-controlled diastereoselectivity switch in formation of dihydropyrans2018

    • Author(s)
      丸山浩紀、本間千裕、加納太一、丸岡啓二
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Chiral amine-catalyzed asymmetric conjugate addition of aldehydes to α-phenylselenoenones as formal Z-allylating agents2018

    • Author(s)
      本間千裕、丸山浩紀、加納太一、丸岡啓二
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Asymmetric Synthesis of Tritylpyrrolidine Derivatives and Their Application to Asymmetric Benzoyloxylation2018

    • Author(s)
      下垣実央、丸山浩紀、本間千裕、加納太一、丸岡啓二
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Z-ケチミンを利用したα位に四置換炭素を有するアミンの不斉合成2017

    • Author(s)
      青田雄介、加納太一、丸岡啓二
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      2017-03-16
    • Related Report
      2015 Annual Research Report
  • [Presentation] Stereoselective Synthesis of Z-Ketimine and Their Application to Asymmetric Reactions2017

    • Author(s)
      本間千裕、加納太一、丸岡啓二
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      2017-03-16
    • Related Report
      2015 Annual Research Report
  • [Presentation] 光学活性アミンの不斉合成を指向した(Z)-ケチミンの立体選択的合成法の開発2016

    • Author(s)
      加納太一
    • Organizer
      分子研研究会「若い世代が創る次世代型分子触媒の開発とその展望」
    • Place of Presentation
      分子科学研究所
    • Year and Date
      2016-11-10
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Rate acceleration of solid-liquid phase-transfer catalysis by rotor-stator homogenizer2016

    • Author(s)
      Yusuke Aota, Taichi Kano and Keiji Maruoka
    • Organizer
      The International Symposium on Homogeneous Catalysis
    • Place of Presentation
      京都テルサ
    • Year and Date
      2016-07-10
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Boc保護アミナールからのイミン形成と応用2016

    • Author(s)
      加納太一
    • Organizer
      第1回分子性触媒若手セミナー
    • Place of Presentation
      立教大学
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 二級アミン触媒を用いた不斉ヒドロキシアミノ化反応の開発2014

    • Author(s)
      白水文貴、加納太一、丸岡啓二
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-03-27 – 2014-03-30
    • Related Report
      2013 Annual Research Report

URL: 

Published: 2013-05-21   Modified: 2019-03-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi