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2013 Fiscal Year Final Research Report

Innovation of the Asymmetric Reactions by Means of Chiral Bronsted Acid

Research Project

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Project/Area Number 23350046
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

AKIYAMA TAKAHIKO  学習院大学, 理学部, 教授 (60202553)

Project Period (FY) 2011-04-01 – 2014-03-31
Keywords有機分子触媒 / キラルブレンステッド酸 / 不斉合成 / 不斉還元 / 触媒 / リン酸
Research Abstract

Development of an efficient method for the preparation of the desired compounds is an important task in the fields of chemistry because it will lead to the preservation of the environment of the earth and will avoid wasting natural resources. We already reported that chiral phosphoric acid derived from (R)-BINOL functioned as an efficient chiral Bronsted acid catalyst. In this study, we developed efficient method for the preparation of a number of synthetically important intermediates which will be employed for the synthesis of biologically important compounds such as agrochemicals and pharmaceuticals.

  • Research Products

    (33 results)

All 2014 2013 2012 2011 Other

All Journal Article (14 results) Presentation (12 results) Book (6 results) Remarks (1 results)

  • [Journal Article] Stereoselective Construction of All Carbon Quaternary Center by Means of Chiral Phosphoric Acid : Highly Enantioselective Friedel-Crafts Reaction of Indoles with β,β-Disubstituted Nitoroalkenes2014

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

      Chem. Sci

      Volume: 5 Pages: 1799-1803

    • DOI

      10.1039/C3SC53542H

  • [Journal Article] Enantioselective Fluorination of β-Ketoesters Catalyzed by Chiral Sodium Phosphate : Remarkable Enhancement of Reactivity by Simultaneous Utilization of Metal Enolate and Metal Phosphate2014

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

      Chem. Lett

      Volume: 43 Pages: 137-139

    • DOI

      10.1246/cl.130934

  • [Journal Article] Chiral Copper(II) Phosphate Catalyzed Enantioselective Synthesis of Isochromene Derivatives by Sequential Intramolecular Cyclization and Asymmetric Transfer Hydrogenation of o-Alkynylacetophenones2013

    • Author(s)
      Saito, K.; Kajiwara, Y.; Akiyama, T. Angew
    • Journal Title

      Chem. Int. Ed

      Volume: 52 Pages: 13284-13288

    • DOI

      10.1002/anie.201308303

  • [Journal Article] Enantioselective Transfer Hydrogenation of Difluoromethyl Ketimines Using Benzothiazoline as a Hydrogen Donor in Combination with Chiral Phosphoric Acid2013

    • Author(s)
      Sakamoto, T.; Horiguchi, K.; Saito, K.; Mori, K.; Akiyama, T
    • Journal Title

      Asian J. Org. Chem

      Volume: 2 Pages: 943-946

    • DOI

      10.1002/ajoc.201300174

  • [Journal Article] Prediction of Suitable Catalyst by 1H NMR : Asymmetric Synthesis of Multisubstituted Biaryls by Chiral Phosphoric Acid Catalyzed Asymmetric Bromination2013

    • Author(s)
      Mori, K.; Ichikawa, Y.; Kobayashi, M.; Shibata, Y.; Yamanaka, M.; Akiyama, T
    • Journal Title

      Chem. Sci

      Volume: 4 Pages: 4235-4239

    • DOI

      10.1039/C3SC52142G

  • [Journal Article] Chiral Phosphoric Acid Catalyzed Oxidative Kinetic Resolution of Indolines Based on Transfer Hydrogenation to Imines2013

    • Author(s)
      Saito, K.; Shibata, Y.; Yamanaka, M.; Akiyama, T
    • Journal Title

      J. Am. Chem. Soc

      Volume: 135 Pages: 11740-11743

    • DOI

      10.1021/ja406004q

  • [Journal Article] Enantioselective Synthesis of Multisubstituted Biaryl Skeleton by Chiral Phosphoric Acid Catalyzed Desymmetrization/Kinetic Resolution Sequence2013

    • Author(s)
      Mori, K.; Ichikawa, Y.; Kobayashi, M.; Shibata, Y.; Yamanaka, M.; Akiyama, T
    • Journal Title

      J. Am. Chem. Soc

      Volume: 135 Pages: 3964-3970

    • DOI

      10.1021/ja311902f

  • [Journal Article] Kinetic Resolution in Chiral Brønsted Acid Catalyzed Aldol Reaction : Enantioselective Robinson-type Annulation Reaction2012

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

      Eur. J. Org. Chem

      Pages: 4508-4514

    • DOI

      10.1002/ejoc.201200338

  • [Journal Article] Phosphoric Acid Catalyzed Enantioselective Transfer Deuteration of Ketimines by Use of Benzothiazoline as a Deuterium Donor : Synthesis of Optically Active Deuterated Amines2012

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

      Org. Lett

      Volume: 14 Pages: 3312-3315

    • DOI

      10.1021/ol3012869

  • [Journal Article] Enantioselective Organocatalytic Reductive Amination of Aliphatic Ketones by Benzothiazoline as Hydrogen Donor2012

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

      Chem. Commun

      Volume: 48 Pages: 4573-4575

    • DOI

      10.1039/C2CC31486J

  • [Journal Article] Chiral Phosphoric Acid Catalyzed Transfer Hydrogenation : A Facile Synthetic Access to Highly Optically Active Trifluoromethylated Amines2011

    • Author(s)
      Henseler, A.; Kato, M.; Mori, K.; Akiyama, T
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 8180-8183

    • DOI

      10.1002/anie.201103240

  • [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

      Volume: 133 Pages: 6166-6169

    • DOI

      10.1021/ja2014955

  • [Journal Article] Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of β-Amino-α,α-difluoro Carbonyl Compounds2011

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

      Org. Lett

      Volume: 13 Pages: 1860-1863

    • DOI

      10.1021/ol200374m

  • [Journal Article] Chiral Phosphoric Acid Catalyzed Transfer Hydrogenation of Ketimine Derivatives; Remarkable Difference in Enantioselectivity depending on Hydrogen donors

    • Author(s)
      Saito, K.; Horiguchi, K.; Shibata, Y.; Yamanaka, M.; Akiyama, T
    • Journal Title

      Chem. Eur. J. Early View

    • DOI

      10.1002/chem.201402763

  • [Presentation] Oxidative Kinetic Resolution of Indolines based on Transfer Hydrogenation to Ketimines by means of Chiral Phosphoric Acid2013

    • Author(s)
      Akiyama, T.; Saito, K
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2013 (C&FC 2013), (Renmin University of China)
    • Place of Presentation
      Beijing, China
    • Year and Date
      20131201-05
  • [Presentation] Oxidative Kinetic Resolution of Indolines base on Transfer Hydrogenation of Ketimines by means of Chiral Phoshoric Acid2013

    • Author(s)
      Akiyama, T.; Saito, K
    • Organizer
      The 11th International Symposium on Organic Reactions (ISOR 2011 Taipei)
    • Place of Presentation
      Taipei, Taiwan
    • Year and Date
      20131119-22
  • [Presentation] キラルブレンステッド酸触媒反応の新展開2013

    • Author(s)
      秋山隆彦
    • Organizer
      第30回有機合成セミナー
    • Place of Presentation
      瀬戸内児島ホテル ,倉敷, 岡山
    • Year and Date
      20130917-19
  • [Presentation] Enantioselective Transfer Hydrogenation of Ketimines by Use of Benzothiazoline as a Hydrogen Donor2013

    • Author(s)
      秋山隆彦
    • Organizer
      文部科学省科学研究費補助金「新学術領域研究(研究領域提案型)」「有機分子触媒による未来型分子変換」第1回国際会議(兼)第6回有機触媒シンポジウム
    • Place of Presentation
      大津プリンスホテル, 大津
    • Year and Date
      20130527-28
  • [Presentation] キラルブレンステッド酸触媒を用いた不斉合成反応2013

    • Author(s)
      秋山隆彦
    • Organizer
      Symposium on Molecular Chirality 2013,第20回記念シンポジウム モレキュラー・キラリティー2013
    • Place of Presentation
      京都大学, 京都
    • Year and Date
      20130510-11
  • [Presentation] キラルリン酸触媒による非対称化/速度論的光学分割を伴う不斉臭素化反応を鍵とする光学活性ビアリールの不斉合成研究2012

    • Author(s)
      森啓二・市川夕貴・小林真奈人・柴田幸大・山中正浩・秋山隆彦
    • Organizer
      第101回有機合成シンポジウム
    • Place of Presentation
      東京(慶應義塾大学薬学部)
    • Year and Date
      20120606-07
  • [Presentation] Enantioselective Transfer Hydrogenation by Use of Benzothiazoline2012

    • Author(s)
      Akiyama, T.
    • Organizer
      Japan-US Organocatalytic Symposium in Hawaii 2012
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2012-12-17
  • [Presentation] Enantioselective Transfer Hydrogenation of Ketimines by Means of Benzothiazoline as Novel Hydrogen Donor2011

    • Author(s)
      Akiyama, T
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2011 (C&FC2011). Nara Prefectual New Public Hall
    • Place of Presentation
      Nara
    • Year and Date
      2011-12-08
  • [Presentation] Recent Progress in the Chiral Phosphoric Acid Catalyzed Reactions2011

    • Author(s)
      Akiyama, T
    • Organizer
      10th International Symposium on Organic Reactions (ISOR 10). Keio University
    • Place of Presentation
      Yokohama
    • Year and Date
      2011-11-24
  • [Presentation] Chiral Phosphoric Acid Catalyzed C(sp3)-H Bond Activation"2011

    • Author(s)
      Akiyama, T.
    • Organizer
      First German-Japan Organocatalytic Symposium
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2011-10-15
  • [Presentation] Oxidative Kinetic Resolution of Indolines based on Transfer Hydrogenation to Ketimines by means of Chiral Phosphoric Acid

    • Author(s)
      Akiyama, T.
    • Organizer
      Asymmetric Synthesis Conference (Zing Conference)
    • Place of Presentation
      Nerja, Spain
    • Year and Date
      00000225-28
  • [Presentation] Development of Enantioselective Reactions Catalyzed by Chiral Phosphoric Acid

    • Author(s)
      Akiyama T.
    • Organizer
      Indo-Japanese Conference on Process Chemistry R&D
    • Place of Presentation
      Juhu Mumbai, India
    • Year and Date
      00000130-31
  • [Book] The Bimolecular and Intramolecular Mannich and Related Reactions, in Comprehensive Organic Synthesis, 2nd Edition, Volume 2, Edited by Molander, G. A.; Knochel, P. Oxford2014

    • Author(s)
      Akiyama, T
    • Total Pages
      629-681
    • Publisher
      Elsevier
  • [Book] Brønsted Acids : Chiral Phosphoric Acid Catalys in Asymmetric Synthesis, in Volume 2, Comprehensive Enantioselecitve Organocatalysis, Edited by Dalko, P. I. Wiley-VCH2013

    • Author(s)
      Mori, K.; Akiyama, T.
    • Total Pages
      289-314
    • Publisher
      Weinheim, Germany
  • [Book] Phosphoric Acid Catalyzed Reactions of Imines, Section 2.1.1. Asymmetric Organocatalysis, Science of Synthesis, Edited by Maruoka, K. Georg Thime Verlag KG2012

    • Author(s)
      Akiyama, T
    • Total Pages
      169-217
    • Publisher
      Stuttgart, Germany
  • [Book] Synthesis without Metals, in "Handbook of Green Chemistry, Edited by Li, C.-J. Wiley-VCH2012

    • Author(s)
      Akiyama, T
    • Total Pages
      307-334
    • Publisher
      Weinheim, Germany
  • [Book] Asymmetric C-C Bond Formation Using Chiral Phoshoric Acid, in Asymetric Synthesis II, Edited by Christmann, M.; Bräse, S. Wiley-VCH2012

    • Author(s)
      Akiyama, T
    • Total Pages
      261-266
    • Publisher
      Weinheim, Germany
  • [Book] 6.3 C-C Bond Formation : Mannich Reaction, in Volume 6: Synthetic Methods V -Organocatalysis, Comprehensive Chirality, Edited by Maruoka, K.2012

    • Author(s)
      Akiyama, T
    • Total Pages
      69-96
    • Publisher
      Elsevier
  • [Remarks]

    • URL

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

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Published: 2015-06-25  

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