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Development of Asymmetric Catalysis by Transition Metal Complexes with C-N Bond Axial Chirality

Research Project

Project/Area Number 22750082
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionChiba University

Principal Investigator

MINO Takashi  千葉大学, 大学院・工学研究科, 准教授 (40302533)

Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2012: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2010: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords不斉配位子 / 有機化学 / 不斉合成 / 有機合成 / 合成化学
Research Abstract

We report here the synthesis of C-N bond atropisomers of N-indole type phosphine ligandand acyclic amines. We also report their application as the chiral ligands for suchcatalytic asymmetric reactions as a palladium-catalyzed asymmetric allylic alkylationof malonate. And more, we report the palladium-catalyzed asymmetric allylic alkylationof indoles with 1,3-diphenyl-2-propenyl acetate using C-N bond axially chiral phosphineligands in good yields with moderate to high enantioselectivities.

Report

(4 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (28 results)

All 2013 2012 2011 2010 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (20 results) Remarks (1 results)

  • [Journal Article] Palladium-catalyzed asymmetric allylic alkylation ofindoles by C-N bond axially chiralphosphine ligands2013

    • Author(s)
      Takashi Mino, Miho Ishikawa, Kenji Nishikawa, Kazuya Wakui, Masami Sakamoto
    • Journal Title

      Tetrahedron:Asymm.

      Volume: Vol. 24(印刷中) Issue: 8 Pages: 499-504

    • DOI

      10.1016/j.tetasy.2013.03.008

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed Mizoroki-Heck type reaction with aryl trialkoxysilanes using hydrazone ligands2012

    • Author(s)
      Takashi Mino, Masanori Shibuya, Saori Suzuki, Kiminori Hirai, Masami Sakamoto, Tsutomu Fujita
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 2 Pages: 429-432

    • DOI

      10.1016/j.tet.2011.11.027

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 1,3-Diarylpropenes through Palladium-Catalyzed Mizoroki-Heck and Allyl Cross-Coupling Reactions Using Hydrazones as Ligands2012

    • Author(s)
      Masami Sakamoto
    • Journal Title

      Eur.J.Org.Chem.

      Volume: (In press) Issue: 4 Pages: 678-680

    • DOI

      10.1002/ejoc.201101533

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Atropisomerism at C-N Bonds of Acyclic Amines: Synthesis and Application to Palladium-Catalyzed Asymmetric Allylic Alkylations2011

    • Author(s)
      Takashi Mino, Haruka Yamada, ShingoKomatsu, Mizuki Kasai, Masami Sakamoto, and Tsutomu Fujita
    • Journal Title

      Eur. J. Org. Chem

      Volume: 2011 Issue: 24 Pages: 4540-4542

    • DOI

      10.1002/ejoc.201100769

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chiral phosphine-prolineamide as organocatalyst in the direct asymmetric aldol reactions2011

    • Author(s)
      Takashi Mino, Ayaka Omura, Yukari Uda, Kazuya Wakui, Yuri Haga, Masami Sakamoto, Tsutomu Fujita
    • Journal Title

      Tetrahedron : Asymm.

      Volume: 22 Issue: 23 Pages: 2026-2030

    • DOI

      10.1016/j.tetasy.2011.11.021

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] N-Arylindole-derived C-N bond axially chiral phosphine ligands: Synthesis and application in palladium-catalyzed asymmetric allylic alkylation2010

    • Author(s)
      Takashi Mino, Shingo Komatsu, Kazuya Wakui, Haruka Yamada, Hiroaki Saotome, Masami Sakamoto, and Tsutomu Fujita
    • Journal Title

      Tetrahedron: Asymm

      Volume: Vol. 21 Issue: 6 Pages: 711-718

    • DOI

      10.1016/j.tetasy.2010.03.039

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] N-Aryl indole-derived C-N bond axially chiral phosphine ligands : synthesis and application in palladium-catalyzed asymmetric allylic alkylation2010

    • Author(s)
      Takashi Mino, Shingo Komatsu, Kazuya Wakui, Haruka Yamada, Hiroaki Saotome, Masami Sakamoto, Tsutomu Fujita
    • Journal Title

      Tetrahedron : Asymmetry

      Volume: 21 Pages: 711-718

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] 軸不斉キラルアミノホスフィンの合成とパラジウム触媒を用いた不斉アリル位アルキル化反応への応用2013

    • Author(s)
      三野孝・浅川源・山田遥・坂本昌巳
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀)
    • Year and Date
      2013-03-24
    • Related Report
      2012 Final Research Report
  • [Presentation] インドール骨格を有するC-N軸不斉配位子を用いたパラジウム触媒によるインドール類の不斉アリル位アルキル化反応2013

    • Author(s)
      三野孝・石川美穂・西川健士・坂本昌巳
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 軸不斉化合物の合成と触媒的不斉反応への利用2013

    • Author(s)
      三野孝
    • Organizer
      第1回千葉大学キラリティーネットワーク研究会講演会
    • Place of Presentation
      千葉大学(千葉)
    • Year and Date
      2013-03-05
    • Related Report
      2012 Final Research Report
  • [Presentation] 軸不斉キラルアミノホスフィンの合成とパラジウム触媒を用いた不斉アリル位アルキル化反応への応用2013

    • Author(s)
      三野 孝、浅川 源、山田 遥、坂本 昌巳
    • 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 Annual Research Report
  • [Presentation] インドール骨格を有するC-N軸不斉配位子を用いたパラジウム触媒によるインドール類の不斉アリル位アルキル化反応2013

    • Author(s)
      三野 孝、石川美穂、西川健士、坂本昌巳
    • 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 Annual Research Report
  • [Presentation] 軸不斉化合物の合成と触媒的不斉反応への利用2013

    • Author(s)
      三野 孝
    • Organizer
      第1回千葉大学キラリティーネットワーク研究会講演会
    • Place of Presentation
      千葉大学(千葉)
    • Related Report
      2012 Annual Research Report
  • [Presentation] ホスフィン-プロリンアミドを不斉有機触媒として用いた不斉アルドール反応2012

    • Author(s)
      三野孝・芳賀裕理・大村彩夏・坂本昌巳・藤田力
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学・神奈川
    • Year and Date
      2012-03-28
    • Related Report
      2011 Annual Research Report
  • [Presentation] C-N軸不斉配位子を用いたパラジウム触媒によるインドール類の不斉アリル位アルキル化反応への応用2012

    • Author(s)
      三野孝・石川美穂・西川健士・笠井瑞起・坂本昌巳・藤田力
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学(神奈川)
    • Year and Date
      2012-03-27
    • Related Report
      2012 Final Research Report
  • [Presentation] C-N軸不斉配位子を用いたパラジウム触媒によるインドール類の不斉アリル位アルキル化反応への応用2012

    • Author(s)
      三野孝・石川美穂・西川健士・笠井瑞起・坂本昌巳・藤田力
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学・神奈川
    • Year and Date
      2012-03-27
    • Related Report
      2011 Annual Research Report
  • [Presentation] ヒドラゾン-パラジウム触媒によるMizoroki-Heck反応とアリル位アリール化反応による1,3-ジアリールプロペンの合成2012

    • Author(s)
      三野孝・鈴木沙織・平井公徳・小泉知子・梶原賢二・坂本昌巳・藤田力
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学・神奈川
    • Year and Date
      2012-03-27
    • Related Report
      2011 Annual Research Report
  • [Presentation] ヒドラゾン-パラジウム触媒によるアリルエーテルのアリル位アリール化反応による1,3-ジアリールプロペンの合成2012

    • Author(s)
      三野孝・小暮健人・平井公徳・小泉知子・坂本昌巳・藤田力
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学・神奈川
    • Year and Date
      2012-03-27
    • Related Report
      2011 Annual Research Report
  • [Presentation] ヒドラゾン配位子を用いた低触媒量パラジウム触媒によるSonogashira反応2011

    • Author(s)
      鈴木沙織・三野孝・平井公徳・坂本昌巳・藤田力
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学・愛知
    • Year and Date
      2011-09-09
    • Related Report
      2011 Annual Research Report
  • [Presentation] BICMAP配位子を用いたRh触媒によるアリール ボロン酸の不斉1,4-付加反応2011

    • Author(s)
      橋本雅俊・三野孝・上原勝徳・坂本昌巳・藤田力
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学・愛知
    • Year and Date
      2011-09-08
    • Related Report
      2011 Annual Research Report
  • [Presentation] Acyclic chiral amines: Synthesis and application to palladium-catalyzed asymmetric allylic alkylation2011

    • Author(s)
      Takashi Mino, Haruka Yamada, Shingo Komatsu, Mizuki Kasai, Masami Sakamoto,and Tsutomu Fujita
    • Organizer
      242nd ACS National Meeting & Exposition
    • Place of Presentation
      デンバー(米国)
    • Year and Date
      2011-08-31
    • Related Report
      2012 Final Research Report
  • [Presentation] Design of chiral ligands with axially chiral C-N bonds for palladium catalyzed asymmetric reaction2010

    • Author(s)
      Takashi Mino, Haruka Yamada, Kazuya Wakui, Masami Sakamoto, and Tsutomu Fujita
    • Organizer
      2010 環太平洋国際化学会議
    • Place of Presentation
      ホノルル(米国)
    • Year and Date
      2010-12-17
    • Related Report
      2012 Final Research Report
  • [Presentation] Design of chiral ligands with axially chiral C-N bonds for palladium catalyzed asymmetric reaction2010

    • Author(s)
      Takashi Mino, Haruka Yamada, Kazuya Wakui, Masami Sakamoto, Tsutomu Fujita
    • Organizer
      2010環太平洋国際化学会議
    • Place of Presentation
      ホノルル(米国)
    • Year and Date
      2010-12-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] N-Aryl Indole-Derived Chiral Phosphines for Palladium Catalyzed Asymmetric Reactions2010

    • Author(s)
      Takashi Mino, Haruka Yamada, Shingo Komatsu, Kazuya Wakui, Masami Sakamoto,and Tsutomu Fujita
    • Organizer
      5rd International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      新竹(台湾)
    • Year and Date
      2010-11-09
    • Related Report
      2012 Final Research Report 2010 Annual Research Report
  • [Presentation] 炭素-窒素軸不斉を有するアミノホスフィンの合成と不斉配位子としての利用2010

    • Author(s)
      三野孝
    • Organizer
      2010年度若手研究者のためのセミナー
    • Place of Presentation
      千葉大学(千葉)
    • Year and Date
      2010-09-25
    • Related Report
      2012 Final Research Report
  • [Presentation] N-アリールインドール骨格を有するキラルホスフィンを用いたパラジウム触媒による不斉アリル位アルキル化反応2010

    • Author(s)
      山田遥・三野孝・小松伸吾・涌井和也・坂本昌巳・藤田力
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      中央大学(東京)
    • Year and Date
      2010-09-16
    • Related Report
      2012 Final Research Report
  • [Presentation] N-アリールインドール骨格を有するキラルホスフィンを用いたパラジウム触媒による不斉アリル位アルキル化反応2010

    • Author(s)
      山田遥・三野孝・小松伸吾・涌井和也・坂本昌巳・藤田力
    • Organizer
      第57回 有機金属化学討論会
    • Place of Presentation
      八王子市
    • Year and Date
      2010-09-16
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://chem.tf.chiba-u.jp/gacb06/nonframe_top.html

    • Related Report
      2012 Final Research Report

URL: 

Published: 2010-08-23   Modified: 2019-07-29  

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