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Design of Molecular Catalyst using Alkyl Chain as a Functional Group

Research Project

Project/Area Number 23350017
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

MATSUBARA Seijiro  京都大学, 工学(系)研究科(研究院), 教授 (90190496)

Project Period (FY) 2011-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥20,280,000 (Direct Cost: ¥15,600,000、Indirect Cost: ¥4,680,000)
Fiscal Year 2014: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2013: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2012: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2011: ¥8,580,000 (Direct Cost: ¥6,600,000、Indirect Cost: ¥1,980,000)
Keywords複素環合成 / 有機分子触媒 / 金属ポルフィリン / ニッケル触媒 / 有機亜鉛 / 有機亜鉛反応剤 / リチウム触媒 / 不斉合成 / イソシアナート / 二亜鉛種 / 複素環 / ヘミアセタール / Michael付加 / 不斉反応 / 共役付加
Outline of Final Research Achievements

At the beginning of the project, we focused on the alkyl chain, which has a self-assembling ability and hydrophobicity, and tried to develop highly selective and efficient catalyst. During the research, we found a use of organocatalyst, which has a molecular flame with two functional group, is effective for the preparation of heterocyclic compound with high asymmetric induction. Moreover, we also found a novel cycloaddition reaction using metal-porphiryn catalyst, which has high hydrophobicity. And also, we developed novel method for the preparation of cyclic compounds using nickel catalyst and organozinc reagent.

Report

(5 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • Research Products

    (46 results)

All 2015 2014 2013 2012 2011 Other

All Journal Article (27 results) (of which Peer Reviewed: 27 results,  Acknowledgement Compliant: 12 results,  Open Access: 1 results) Presentation (11 results) (of which Invited: 5 results) Book (1 results) Remarks (7 results)

  • [Journal Article] Preparation of cycloheptane ring by nucleophilic cyclopropanation of 1,2-diketones with bis(iodozincio)methane2015

    • Author(s)
      Ryosuke, H.; Takada, Y.; Matsubara, S.
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 13 Issue: 1 Pages: 241-247

    • DOI

      10.1039/c4ob01474j

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Nickel-catalyzed synthesis of tetrasubstituted vinyl sulfides from thiocarbamates and internal alkynes2015

    • Author(s)
      Tasuku Inami, Takuya Kurahashi, Seijiro Matsubara
    • Journal Title

      Chemical Communications

      Volume: 51 Issue: 7 Pages: 1285-1288

    • DOI

      10.1039/c4cc09123j

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium(III) Porphyrin-catalyzed Reactions via Activation of Alkynes2014

    • Author(s)
      Hasegawa, M.; Kurahashi, T.; Matsubara, S.
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 12 Pages: 1937-1939

    • DOI

      10.1246/cl.140810

    • NAID

      130004703968

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Design of Molecular Transformations Based on the Concerted Function of Two Zinc Atoms in Bis(iodozincio)methane2014

    • Author(s)
      Sada, M.; Uchiyama, M.; Matsubara, S.
    • Journal Title

      Synlett

      Volume: 25 Issue: 20 Pages: 2831-2841

    • DOI

      10.1055/s-0034-1379250

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Nickel-Catalyzed Reaction of Thioisatins and Alkynes: A Facile Synthesis of Thiochromones2014

    • Author(s)
      Inami, T.; Kurahashi, T.; Matsubara, S.
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 21 Pages: 5660-5662

    • DOI

      10.1021/ol5026102

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regio- and Diastereoselective Nickel-Catalyzed Cycloaddition of Activated Cyclopropanes with Allenes2014

    • Author(s)
      Tombe, R.; Iwamoto, T.; Kurahashi, T.; Matsubara, S.
    • Journal Title

      Synlett

      Volume: 25 Issue: 16 Pages: 2281-2284

    • DOI

      10.1055/s-0034-1378371

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Cobalt Porphyrin Catalyzed [3+2] Cycloaddition of Cyclopropanes and Carbonyl Compounds2014

    • Author(s)
      Shiba, Takahiro; Kuroda, Daiki; Kurahashi, T.; Matsubara, S.
    • Journal Title

      Synlett

      Volume: 25 Issue: 14 Pages: 2005-2008

    • DOI

      10.1055/s-0034-1378394

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Lithium(1+)-Catalyzed Nazarov-Type Cyclization of 1-Arylbuta-2,3-dien-1-ols: Synthesis of Benzofulvene Derivatives2014

    • Author(s)
      Sai,M.; Matsubara, S.
    • Journal Title

      Synlett

      Volume: 25 Issue: 14 Pages: 2067-2071

    • DOI

      10.1055/s-0034-1378333

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Preparation of the Zinc Enolate Equivalent of Amides by Zinciomethylation of Isocyanates: Catalytic Asymmetric Reformatsky-Type Reaction2014

    • Author(s)
      Haraguchi, R.; Matsubara, S.
    • Journal Title

      Synthesis

      Volume: 46 Issue: 17 Pages: 2272-2282

    • DOI

      10.1055/s-0034-1378514

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Nickel-Catalyzed Redox-Economical Coupling of Alcohols and Alkynes to Form Allylic Alcohols2014

    • Author(s)
      Nakai, K.; Yoshida, Y.; Kurahashi, T.; Matsubara, S.
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 22 Pages: 7797-7780

    • DOI

      10.1021/ja500666h

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium Porphyrin Catalyzed Hydrogenation of Alkynes: Stereoselective Synthesis of cis-Alkenes2014

    • Author(s)
      Nishibayashi, R.; Kurahashi, T.; Matsubara, S.
    • Journal Title

      Synlett

      Volume: 25 Issue: 09 Pages: 1287-1290

    • DOI

      10.1055/s-0033-1341240

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Diastereoselective Construction of Trans-Fused Octalone Framework via Ruthenium-Porphyrin-Catalyzed Cycloaddition2014

    • Author(s)
      Terada, T.; Kurahashi, T.; Matsubara, S.
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 10 Pages: 2594-2597

    • DOI

      10.1021/ol500625r

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric Isomerization of ω-Hydroxy-α,β-Unsaturated Thioesters into β -Mercaptolactones by a Bifunctional Aminothiourea Catalyst2014

    • Author(s)
      Fukata, Y.; Okamura, T.; Asano, K.; Matsubara, S.
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 8 Pages: 2184-2187

    • DOI

      10.1021/ol500637x

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric Indoline Synthesis via Intramolecular Aza-Michael Addition Mediated by Bifunctional Organocatalysts2013

    • Author(s)
      Miyaji, R.; Asano, K.; Matsubara, S.
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 33 Pages: 3658-3661

    • DOI

      10.1021/ja407027e

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Indoline Synthesis via Intramolecular Aza-Michael Addition Mediated by Bifunctional Organocatalysts2013

    • Author(s)
      Ryota Miyaji, keisuke Asano, Seijiro Matsubara
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 14 Pages: 3658-3661

    • DOI

      10.1021/ol401538b

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron Corrole Catalyzed [4+2] Cycloaddition of Dienes and Aldehydes2013

    • Author(s)
      Kuwano, T.; Kurahashi, T.; Matsubara, S.
    • Journal Title

      Chem. Lett.

      Volume: 42 Issue: 10 Pages: 1241-1243

    • DOI

      10.1246/cl.130672

    • NAID

      10031201324

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cationic Iron(III) Porphyrin Catalyzed Dehydrative Friedel–Crafts Reaction of Alcohols with Arenes2013

    • Author(s)
      Teranishi, S.; Kurahashi, T.; Matsubara, S.
    • Journal Title

      Synlett

      Volume: 24 Issue: 16 Pages: 2148-2152

    • DOI

      10.1055/s-0033-1339640

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Aldol-Type Reaction of Zinc Enolate Equivalent of Amides2013

    • Author(s)
      Haraguchi, R.; Matsubara, S.
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 8 Pages: 3378-3380

    • DOI

      10.1021/ol4005068

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of 1,3-Dioxolanes by Organocatalytic Formal [3+2] Cycloaddition via Hemiacetal Intermediates2012

    • Author(s)
      Asano, K.; Matsubara, S
    • Journal Title

      Org. Lett

      Volume: 14 Issue: 6 Pages: 1620-1623

    • DOI

      10.1021/ol3003755

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organocatalytic Asymmetric Oxy-Michael Addition to a γ-Hydroxy-α,β-Unsaturated Thioester via Hemiacetal Intermediates2012

    • Author(s)
      岡村高明, 浅野圭佑, 松原誠二郎
    • Journal Title

      Chemical Communications

      Volume: 48(Advanced Article) Issue: 42 Pages: 5076-5078

    • DOI

      10.1039/c2cc31602a

    • NAID

      120005244282

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cationic Iron(III) Porphyrin-Catalyzed [4+2] Cycloaddition of Unactivated Aldehydes with Simple Dienes2012

    • Author(s)
      Fujiwara, K.; Kurahashi, T.;Matsubara, S
    • Journal Title

      J. Am. Chem. Soc

      Volume: 134 Issue: 12 Pages: 5512-5515

    • DOI

      10.1021/ja300790x

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rapid Preparation of Cycloheptane Ring from 1,2-Diketone and Bis(iodozincio)methane via Oxy-Cope Rearrangement Using Microflow System2012

    • Author(s)
      Haraguchi, R.; Takada, Y.; Matsubara, S
    • Journal Title

      Chem. Lett

      Volume: 41 Issue: 6 Pages: 628-629

    • DOI

      10.1246/cl.2012.628

    • NAID

      10030620589

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Manganese Porphyrin Catalyzed Cycloisomerization of Enynes2012

    • Author(s)
      Takuya Ozawa
    • Journal Title

      ORGANIC LETTERS

      Volume: 14 Pages: 3008-3011

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cobalt(III) Porphyrin Catalyzed Aza-Diels-Alder Reaction2012

    • Author(s)
      Wakabayashi, R.; Kurahashi, T.; Matsubara, S
    • Journal Title

      Org. Lett

      Volume: 14(18) Issue: 18 Pages: 4794-4797

    • DOI

      10.1021/ol3020946

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Catalytic Cycloetherification Mediated by Bifunctional Organocatalysts2011

    • Author(s)
      浅野圭佑, 松原誠二郎
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Issue: 42 Pages: 16711-16713

    • DOI

      10.1021/ja207322d

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Silver-Catalyzed Intramolecular Chloroamination of Allenes : Easy Access to Functionalized 3-Pyrroline and Pyrrole Derivatives2011

    • Author(s)
      Masahiro Sai, Seijiro Matsubara
    • Journal Title

      Organic Letters

      Volume: 13 Issue: 17 Pages: 4676-4679

    • DOI

      10.1021/ol201895s

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Transition-Metal Chloride Mediated Addition Reaction of Diorganomagnesium to Easily Enolizable Ketones2011

    • Author(s)
      Sada, M.; Matsubara, S.
    • Journal Title

      Tetrahedron.

      Volume: 67 (14) Issue: 14 Pages: 2612-2614

    • DOI

      10.1016/j.tet.2011.02.009

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] アレノンと有機二亜鉛種の反応による1,3-二亜鉛種の調製2015

    • Author(s)
      原口亮介・松原誠二郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Preparation of Arenylmethylzinc Reagent from Iodoarene by Pd/Ni-Catalyzed Cross-Coupling Reaction2015

    • Author(s)
      SHIMADA, Yukako; MATSUBARA, Seijiro
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] 二官能性有機触媒によるシアノヒドリンの不斉分子内オキシマ イケル付加反応2015

    • Author(s)
      米田直紀,浅野圭佑,松原誠二郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] Preparation of Heterocycle Based on Ni-catalyzed C-C Bond Activation2014

    • Author(s)
      Seijiro Matsubara
    • Organizer
      Fifth International Collaborative and Cooperative Chemistry Symposium
    • Place of Presentation
      京都大学理学部吉田キャンパス
    • Year and Date
      2014-09-30
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 有機金属反応剤と有機分子触媒の使い方2014

    • Author(s)
      松原誠二郎
    • Organizer
      第34回有機合成若手セミナー「明日の有機合成を担う人のために」
    • Place of Presentation
      大阪科学技術センター
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Asymmetric Synthesis of Heterocycles using Bifunctional Organocatalysts2013

    • Author(s)
      Seijiro Matsubara
    • Organizer
      The 8th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      大阪
    • Related Report
      2013 Annual Research Report
  • [Presentation] Procedure-Controlled Enantioselectivity Switch in Organocatalytic 2-Oxazolidinone Synthesis2013

    • Author(s)
      Seijiro Matsubara
    • Organizer
      The Eighth International Symposium on Integrated Synthesis
    • Place of Presentation
      奈良
    • Related Report
      2013 Annual Research Report
  • [Presentation] 有機亜鉛反応剤系でのマイクロフローの微分的な利用2012

    • Author(s)
      松原誠二郎
    • Organizer
      フロー・マイクロ合成研究会第26回公開講演会
    • Place of Presentation
      大阪
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 環化付加と環化反応の新しい工夫2012

    • Author(s)
      松原誠二郎
    • Organizer
      平成24年度後期有機合成化学講習会
    • Place of Presentation
      東京
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Novel Synthetic Method for Heterocyclic Compounds2012

    • Author(s)
      松原誠二郎
    • Organizer
      Bristol-Kyoto Organic Synthesis Workshop in Kyoto
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] New Methods for the Preparation of Heterocyclic Compounds2011

    • Author(s)
      Seijiro Matsubara
    • Organizer
      2nd International Collaborative and Cooperative Chemistry Symposium (ICCCS2)
    • Place of Presentation
      豪・The University of Queensland(招待講演)
    • Year and Date
      2011-11-01
    • Related Report
      2011 Annual Research Report
  • [Book] 有機合成化学2012

    • Author(s)
      松原誠二郎(共著)
    • Total Pages
      394
    • Publisher
      東京化学同人
    • Related Report
      2011 Annual Research Report
  • [Remarks] 松原誠二郎ー研究者ーreseachmap

    • URL

      http://researchmap.jp/read0012787/

    • Related Report
      2014 Annual Research Report
  • [Remarks] 有機合成の新手法の開発

    • URL

      http://www.dfm.kuic.kyoto-u.ac.jp/Website/Research.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] Publication

    • URL

      http://www.dfm.kuic.kyoto-u.ac.jp/Website/Publication.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] 松原研研究内容

    • URL

      http://www.dfm.kuic.kyoto-u.ac.jp/Website/Research.html

    • Related Report
      2013 Annual Research Report
  • [Remarks] 松原研成果論文

    • URL

      http://www.dfm.kuic.kyoto-u.ac.jp/Website/Publication.html

    • Related Report
      2013 Annual Research Report
  • [Remarks] 京都大学大学院工学研究科材料化学専攻有機反応化学分野松原研究室

    • URL

      http://www.dfm.kuic.kyoto-u.ac.jp/Website/Welcome.html

    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.dfm.kuic.kyoto-u.ac.jp/Website/Welcome.html

    • Related Report
      2011 Annual Research Report

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Published: 2011-04-06   Modified: 2019-07-29  

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