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2009 Fiscal Year Final Research Report

Development of Chiral Bronsted Acid Catalysts

Research Project

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Project/Area Number 19350026
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionGakushuin University

Principal Investigator

AKIYAMA Takahiko  Gakushuin University, 理学部, 教授 (60202553)

Project Period (FY) 2007 – 2009
Keywords不斉合成 / 有機合成化学 / 触媒 / エナンチオ選択性 / リン酸 / キラルブレンステッド酸 / 有機触媒
Research Abstract

Asymmetric reactions by means of chiral phosphoric acid derived from (R)-BINOL as chiral Bronsted acid were investigated. Transfer hydrogenation reaction was achieved by use of a novel hydrogen donor. In order to expand the scope of the chiral phosphoric acid catalyzed reactions, intramolecular aldol reaction was studied and the corresponding cyclohexenone were obtained with excellent enantioselectivities.

  • Research Products

    (43 results)

All 2011 2010 2009 2008 2007 Other

All Journal Article (20 results) Presentation (18 results) Book (3 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Selective Activation of Enantiotopic C(sp3)-Hydrogen by Means of a Chiral Phosphoric Acid : Asymmetric Synthesis of Chiral Tetrahydroquinoline Derivatives2011

    • Author(s)
      Mori, K.; Ehara, K.; Kurihara, K.; Akiyama, T.
    • Journal Title

      J.Am.Chem.Soc. 133(16)

      Pages: 6166-6169

  • [Journal Article] Chiral Bronsted Acid-Catalyzed Asymmetric Friedel-Crafts Alkylation of Indoles with α,β-Unsaturated Ketones : Short Access to Optically Active 2-and 3-Substituted Indole Derivatives2010

    • Author(s)
      Sakamoto, T.; Itoh, J.; Mori, K.; Akiyama T.
    • Journal Title

      Org.Biomol.Chem. 8(23)

      Pages: 5448-5454

  • [Journal Article] Benzothiazoline : Highly Efficient Reducing Agent for the Enantioselective Organocatalytic Transfer Hydrogenation of α-Imino Esters2010

    • Author(s)
      Zhu, C.; Akiyama, T.
    • Journal Title

      Adv.Synth.Catal. 352(11-12)

      Pages: 1846-1850

  • [Journal Article] Enantioselective Friedel-Crafts Alkylation Reaction of Indoles with Unsaturated Acyl Phosphonates Catalyzed by a Chiral Phosphoric Acid2010

    • Author(s)
      Bachu, P.; Akiyama, T.
    • Journal Title

      Chem.Commun. 46(23)

      Pages: 4112-4114

  • [Journal Article] Expeditious Synthesis of Benzopyrans via Lewis Acid Catalyzed C-H Functionalization : Remarkable Enhancement of Reactivity by Ortho-Substituent2010

    • Author(s)
      Mori, K.; Kawasaki, T.; Sueoka, S.; Akiyama, T.
    • Journal Title

      Org.Lett. 12(8)

      Pages: 1732-1735

  • [Journal Article] Enantioselective Friedel-Crafts Alkylation of Indoles, Pyrroles, and Furans with 3, 3, 3-Trifluoropyruvate Catalyzed by Chiral Phosphoric Acid2010

    • Author(s)
      Kashikura, W.; Itoh, J.; Mori, K.; Akiyama, T.
    • Journal Title

      Chem.Asian J. 5(3)

      Pages: 470-472

  • [Journal Article] Chiral Phosphoric Acid Catalyzed Desymmetrization of meso-1, 3-Diones: Asymmetric Synthesis of Chiral Cyclohexenones2009

    • Author(s)
      Mori, K.; Katoh, T.; Suzuki, T.; Noji, T.; Yamanaka, M.; Akiyama, T.
    • Journal Title

      Angew.Chem.Int.Ed. 48(51)

      Pages: 9652-9654

  • [Journal Article] Benzothiazoline : Highly Efficient Reducing Agent for the Enantioselective Organocatalytic Transfer Hydrogenation of Ketimines2009

    • Author(s)
      Zhu, C.; Akiyama, T.
    • Journal Title

      Org.Lett. 11(18)

      Pages: 4180-4183

  • [Journal Article] Bronsted Acid-catalyzed Nazarov Cyclization of Pyrrole Derivatives by Microwave Acceleration2009

    • Author(s)
      Bachu,P.; Akiyama, T.
    • Journal Title

      Bioorg.Med.Chem.Lett. 19(14)

      Pages: 3764-3766

  • [Journal Article] Chiral Bronsted Acid Catalyzed Hydrophosphonylation of Aldimines : DFT Study on the Effect of Substituents on thePhosphoric Acid2009

    • Author(s)
      Akiyama, T.; Morita, H.; Bachu, P.; Mori, K.; Yamanaka, M.; Hirata, T.
    • Journal Title

      Tetrahedron 65(26)

      Pages: 4950-4956

  • [Journal Article] Enantioselective Mannich-type Reaction Catalyzed by a Chiral Phosphoric Acid Bearing (S)-Biphenol Backbone2009

    • Author(s)
      Akiyama, T.; Katoh, T.; Mori, K.; Kanno, K.
    • Journal Title

      Synlett 10

      Pages: 1664-1666

  • [Journal Article] Dual Functionalization of Allene : Facile Construction of Heteropolycycles Catalyzed by Bronsted Acid2009

    • Author(s)
      Mori, K.; Sueoka, S.; Akiyama, T.
    • Journal Title

      Chem.Lett. 38(6)

      Pages: 628-629

  • [Journal Article] Concise Construction of Quinazolines via Bronsted Acid Induced C-H Activation : Further Extensions of the "tert-Amino Effect"2009

    • Author(s)
      Mori, K.; Ohshima, Y.; Ehara, K.; Akiyama, T.
    • Journal Title

      Chem.Lett. 38(6)

      Pages: 524-525

  • [Journal Article] Enantioselective Aza Darzens Reaction Catalyzed by a Chiral Phosphoric Acid2009

    • Author(s)
      Akiyama, T.; Suzuki, T.; Mori, K.
    • Journal Title

      Org.Lett. 11(11)

      Pages: 2445-2447

  • [Journal Article] Enantioselective Robinson-type Annulation Reaction Catalyzed by Chiral Phosphoric Acid2009

    • Author(s)
      Akiyama, T.; Katoh, T.; Mori, K.
    • Journal Title

      Angew.Chem.Int.Ed. 48(23)

      Pages: 4226-4228

  • [Journal Article] Chiral Phosphoric Acid Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with Nitroalkenes-Cooperative Effect of MS 3A2008

    • Author(s)
      Itoh, J.; Fuchibe, K.; Akiyama, T.
    • Journal Title

      Angew.Chem.Int.Ed. 47(21)

      Pages: 4016-4018

  • [Journal Article] Preparation of β-Amino Esters by Chiral Bronsted Acid-Catalyzed Mannich-type Reaction2008

    • Author(s)
      Itoh, J.; Fuchibe, K.; Akiyama, T.
    • Journal Title

      Synthesis 8

      Pages: 1319-1322

  • [Journal Article] Vinylogous Mannich-type Reaction Catalyzed by an Iodine-Substituted Chiral Phosphoric Acid2008

    • Author(s)
      Akiyama, T.; Honma, Y.; Itoh, J.; Fuchibe, K.
    • Journal Title

      Adv.Synth.Catal. 350(3)

      Pages: 399-402

  • [Journal Article] Stronger Bronsted Acid2007

    • Author(s)
      Akiyama, T.
    • Journal Title

      Chem.Rev. 107(12)

      Pages: 5744-5758

  • [Journal Article] Chiral Bronsted Acid Catalyzed Enantioselective Mannich-type Reaction2007

    • Author(s)
      Yamanaka, M.; Itoh, J.; Fuchibe,K.; Akiyama, T.
    • Journal Title

      J.Am.Chem.Soc. 129(21)

      Pages: 6756-6764

  • [Presentation] Chiral Bronsted Acid-Catalyzed Asymmetric Reactions2010

    • Author(s)
      秋山隆彦
    • Organizer
      11th Florida IUPAC-Sponsored Heterocyclic & Synthetic Conference
    • Place of Presentation
      University of Florida, Gainesville, Florida, USA (Invited Lecture)
    • Year and Date
      20100307-20100310
  • [Presentation] キラルブレンステッド酸触媒を用いた不斉合成の新展開2010

    • Author(s)
      秋山隆彦
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山大学,岡山
    • Year and Date
      2010-03-29
  • [Presentation] キラルブレンステッド酸触媒を用いた不斉合成の新展開:弱い相互作用による立体制御2010

    • Author(s)
      秋山隆彦
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学,東大阪
    • Year and Date
      2010-03-26
  • [Presentation] Chiral Bronsted Acid-Catalyzed Asymmetric Reactions2010

    • Author(s)
      秋山隆彦
    • Organizer
      International Conference in Chemistry, Chem 06,"Contemporary Chemistry and Environment"
    • Place of Presentation
      Cairo University, Cairo, Egypt. (Plenary Lecture)
    • Year and Date
      2010-03-01
  • [Presentation] Chiral Bronsted Acid-Catalyzed Asymmetric Reactions2009

    • Author(s)
      秋山隆彦
    • Organizer
      The 13th Asian Chemical Congress
    • Place of Presentation
      Shanghai, China
    • Year and Date
      20090914-20090916
  • [Presentation] Chiral Bronsted Acid-Catalyzed Asymmetric Reactions2009

    • Author(s)
      秋山隆彦
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2009
    • Place of Presentation
      Korea University, Seoul, Korea
    • Year and Date
      2009-12-14
  • [Presentation] キラルブレンステッド酸触媒を用いた不斉合成-弱い相互作用による立体制御2009

    • Author(s)
      秋山隆彦
    • Organizer
      第58回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      長岡科学技術大学
    • Year and Date
      2009-11-28
  • [Presentation] キラルブレンステッド酸触媒を用いた不斉合成-弱い相互作用による立体制御2009

    • Author(s)
      秋山隆彦
    • Organizer
      プロセス化学を指向する精密合成化学シンポジウム
    • Place of Presentation
      京都テルサ
    • Year and Date
      2009-06-01
  • [Presentation] キラルブレンステッド酸触媒の開発と不斉合成反応への展開2009

    • Author(s)
      秋山隆彦
    • Organizer
      第5回筑波大学学際物質科学研究センター機能性分子シンポジウム
    • Place of Presentation
      筑波大院数理物質科学
    • Year and Date
      2009-02-21
  • [Presentation] キラルブレンステッド酸触媒を用いた含窒素化合物の不斉合成2009

    • Author(s)
      秋山隆彦
    • Organizer
      第14回精密合成化学セミナー
    • Place of Presentation
      北大院
    • Year and Date
      2009-01-09
  • [Presentation] Chiral Bronsted Acid-Catalyzed Enantioselective Synthesis of Nitrogen-containing Compounds2008

    • Author(s)
      秋山隆彦
    • Organizer
      The 9th International Symposium on Organic Reactions
    • Place of Presentation
      Chiayi, Taiwan
    • Year and Date
      20081120-20081123
  • [Presentation] キラルブレンステッド酸触媒を用いた含窒素化合物の不斉合成2008

    • Author(s)
      秋山隆彦
    • Organizer
      第23回農薬デザイン研究会
    • Place of Presentation
      大手町サンスカイルーム(東京)
    • Year and Date
      2008-11-06
  • [Presentation] キラルブレンステッド酸触媒を用いた含窒素化合物の不斉合成2008

    • Author(s)
      秋山隆彦
    • Organizer
      有機合成化学協会関東支部ミニシンポジウム
    • Place of Presentation
      東京農工大(東京)
    • Year and Date
      2008-09-12
  • [Presentation] Chiral Bronsted Acid-catalyzed Asymmetric Aza Diels-Alder Reactions2007

    • Author(s)
      秋山隆彦
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2007
    • Place of Presentation
      Nanyang Technological University, Singapore
    • Year and Date
      20071217-20071221
  • [Presentation] キラルブレンステッド酸触媒を用いた不斉合成反応2007

    • Author(s)
      秋山隆彦
    • Organizer
      日本化学会第1回関東支部大会
    • Place of Presentation
      東京(首都大学東京)
    • Year and Date
      20070927-20070928
  • [Presentation] キラルブレンステッド酸触媒を用いた不斉合成2007

    • Author(s)
      秋山隆彦
    • Organizer
      プロセス化学会サマーシンポジウム
    • Place of Presentation
      東京
    • Year and Date
      20070802-20070803
  • [Presentation] キラルブレンステッド酸触媒を用いた不斉合成2007

    • Author(s)
      秋山隆彦
    • Organizer
      前期(春季)有機合成化学講習会
    • Place of Presentation
      東京
    • Year and Date
      20070620-20070621
  • [Presentation] Chiral Bronsted Acid-catalyzed Asymmetric Aza Diels-Alder Reactions, 2nd International Conference on Advanced Organic Synthesis Directed toward the Ultimate Efficiency andPracticability2007

    • Author(s)
      秋山隆彦
    • Organizer
      International Conference on Asymmetric Organocatalysis
    • Place of Presentation
      Ohtsu, Japan
    • Year and Date
      20070528-20070529
  • [Book] キラルBronsted酸触媒,進化を続ける有機触媒,丸岡啓二編2009

    • Author(s)
      秋山隆彦
    • Total Pages
      95-104
    • Publisher
      化学同人
  • [Book] Chiral Bronsted Acid, in "Acid Catalysis in Modern Organic Synthesis", Edited by H. Yamamoto, K. Ishihara, Weinheim, Germany2008

    • Author(s)
      秋山隆彦
    • Total Pages
      62-107
    • Publisher
      Wiley-VCH
  • [Book] キラルブレンステッド酸触媒を用いた不斉合成反応,ファインケミカル37(5)2008

    • Author(s)
      秋山隆彦
    • Total Pages
      68-76
    • Publisher
      CMC出版
  • [Remarks] ホームページ等

    • URL

      http://www-cc.gakushuin.ac.jp/~940020/akiyama_site/

  • [Patent(Industrial Property Rights)] 光学活性ビフェニルリン酸誘導体2008

    • Inventor(s)
      菅野和明, 竹原潤, 高井正樹, 秋山隆彦
    • Industrial Property Rights Holder
      三菱化学株式会社
    • Industrial Property Number
      特願2008-210859
    • Filing Date
      2008-08-19

URL: 

Published: 2012-01-26   Modified: 2016-04-21  

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