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2011 Fiscal Year Final Research Report

Chiral Memory Using the Property of Organic Crystals

Research Project

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Project/Area Number 21350024
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

SAKAMOTO Masami  千葉大学, 大学院・工学研究科, 教授 (00178576)

Project Period (FY) 2009 – 2011
Keywords有機光化学 / 有機合成化学 / 不斉合成 / 有機結晶
Research Abstract

New absolute asymmetric synthesis using the property of organic crystals were developed. Crystallization under various conditions was examined and was clarified a change of molecular structure, polymorphism and the crystal structure. Furthermore, I succeeded in controlling the rate of racemization of the apparent chiral molecules in the chiral crystals, and leading it effectively to the optically active products. I also developed the highly diastereoselective reaction using chiral memory controlled by crystallization induced diastereomer transformation (CIDT).

  • Research Products

    (56 results)

All 2012 2011 2010 2009

All Journal Article (19 results) (of which Peer Reviewed: 17 results) Presentation (35 results) Book (2 results)

  • [Journal Article] Two-step Asymmetric Reaction Using the Frozen Chirality Generated by Spontaneous Crystallization2012

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      Org. Lett

      Volume: 14 Pages: 2638-2641

    • DOI

      DOI:10.1021/ol301033r

    • Peer Reviewed
  • [Journal Article] Photocycloaddition Reaction of Methyl 2-and 3-Chromonecarboxylates with Various Alkenes2012

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      Res. Chem. Intermed

    • DOI

      DOI:10.1007/s11164-012-0656-0

    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed Mizoroki-Heck type reaction with aryl trialkoxysilanes using hydrazone ligands2012

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 429-432

    • URL

      http://www.sciencedirect.com/science/journal/00404020/68/2

  • [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, et al
    • Journal Title

      Eur. J. Org. Chem

      Pages: 678-680

    • URL

      http://onlinelibrary.wiley.com/doi/10.1002/ejoc.v2012.4/issuetoc

    • Peer Reviewed
  • [Journal Article] Super Flexibility of a 2D Cu-Based Porous Coordination Framework on Gas Adsorption in Comparison with a 3D Framework of Identical Composition : Framework Dimensionality-Dependent Gas Adsorptivities2011

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      J.Am. Chem. Soc

      Volume: 133 Pages: 10512-10522

    • DOI

      10.1021/ja201170c

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Cyanation of Aryl Bromides Using Phosphine-Free Pyridyl-Hydrazone Ligands2011

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      Heterocycles

      Volume: 83(1) Pages: 163-169

    • URL

      http://www.heterocycles.jp/index.php

    • Peer Reviewed
  • [Journal Article] Kinetic resolution of racemic amines using provisional molecular chirality generated by spontaneous crystallization2011

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      Chem. Commun

      Volume: 47 Pages: 4267-4269

    • DOI

      DOI:10.1039/C1CC00081K

    • Peer Reviewed
  • [Journal Article] Hydrazone Promoted Sonogashira Coupling Reaction with Aryl Bromides at Low Palladium Loadings2011

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      Synlett

      Pages: 1277-1280

    • URL

      https://www.thieme-connect.com/ejournals/toc/synlett

    • Peer Reviewed
  • [Journal Article] Asymmetric photocycloaddition of naphthamide with a diene using the provisional molecular chirality in a chiral crystal2011

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      Photochemical & Photobiological Sciences

      Volume: 10 Pages: 1387-1389

    • URL

      http://pubs.rsc.org/en/journals/journalissues/

    • Peer Reviewed
  • [Journal Article] Asymmetric Intramolecular Cyclobutane Formation via Photochemical Reaction of N,N-Diallyl-2-quinolone-3-carboxamide Using a Chiral Crystalline Environment2011

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 6168-6171

    • DOI

      DOI:10.1021/ol2028652

    • Peer Reviewed
  • [Journal Article] Chiral phosphine-proline amide as organocatalyst in the direct asymmetric aldol reactions2011

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      Tetrahedron : Asymm

      Volume: 22 Pages: 2026-2030

    • URL

      http://www.sciencedirect.com/science/journal/09574166/22/23

    • Peer Reviewed
  • [Journal Article] ラセミ化優先晶出による不斉の発現と増幅2011

    • Author(s)
      坂本昌巳
    • Journal Title

      化学工業, ChemicalIndustry

      Volume: 62 Pages: 53-57

    • URL

      http://www.kako-sha.co.jp/

    • Peer Reviewed
  • [Journal Article] Atropisomerism at C.N Bonds of Acyclic Amines : Synthesis and Application to Palladium-Catalyzed Asymmetric Allylic Alkylations2010

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      Eur. J. Org. Chem

      Pages: 4540-4542

    • URL

      http://onlinelibrary.wiley.com/doi/10.1002/ejoc.v2011.24/issuetoc

  • [Journal Article] 結晶化による不斉の発現と制御:均一系不斉反応への展開2010

    • Author(s)
      坂本昌巳, 他
    • Journal Title

      有機合成化学協会誌

      Volume: 68 Pages: 1047-1056

    • URL

      http://www.jstage.jst.go.jp/browse/yukigoseikyokaishi/-char/ja

    • Peer Reviewed
  • [Journal Article] Amidation of alcohols with nitriles unders olvent-free conditions using molecular iodine as a catalyst2010

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      J. Oleo Science

      Volume: 59 Pages: 607-613

    • URL

      http://www.jstage.jst.go.jp/browse/jos/-char/ja/

    • Peer Reviewed
  • [Journal Article] Synthesis of cinnamyl ethers from α-vinylbenzyl alcohol using iodine as catalyst2010

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      J. Oleo Science

      Volume: 59 Pages: 549-555

    • URL

      http://www.jstage.jst.go.jp/browse/jos/-char/ja/

    • 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)
      Masami Sakamoto, et al
    • Journal Title

      Tetrahedron : Asymm

      Volume: 21 Pages: 711-718

    • URL

      http://www.sciencedirect.com/science/journal/09574166/21/6

    • Peer Reviewed
  • [Journal Article] Exclusive Photodimerization Reactions of Chromone-2-carboxylic Esters Depending on Reaction Media2010

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      Org. Lett

      Volume: 12 Pages: 4435-4437

    • DOI

      DOI:10.1021/ol101734k

    • Peer Reviewed
  • [Journal Article] Photodimerization of chromone2009

    • Author(s)
      Masami Sakamoto, et al
    • Journal Title

      Chem. Commun

      Pages: 2379-2380

    • DOI

      DOI:10.1039/B822829A

    • Peer Reviewed
  • [Presentation] キラルメモリー効果を利用したタンデム不斉反応2012

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会第92春期年会
    • Place of Presentation
      東京
    • Year and Date
      2012-03-25
  • [Presentation] クロモンの光ニ量化反応を利用したC2キラル不斉配位子の開発2012

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会第92春期年会
    • Place of Presentation
      東京
    • Year and Date
      2012-03-25
  • [Presentation] 2-クロモンカルボン酸誘導体の分子内[2+2]光環化付加反応2012

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会第92春期年会
    • Place of Presentation
      東京
    • Year and Date
      2012-03-25
  • [Presentation] キラルな塩形成によるキノロンアミドの軸不斉の制御とキラルメモリーの創製2012

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会第92春期年会
    • Place of Presentation
      東京
    • Year and Date
      2012-03-25
  • [Presentation] β-アロイルアクリル酸誘導体の光異性化を用いた液晶配向制御2012

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会第92春期年会
    • Place of Presentation
      東京
    • Year and Date
      2012-03-25
  • [Presentation] アキラルなニコチンアミド誘導体とキラルな酸との塩形成による軸不斉制御とキラルメモリーの創製2012

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会第92春期年会
    • Place of Presentation
      東京
    • Year and Date
      2012-03-25
  • [Presentation] イソインドリノン誘導体のラセミ化優先晶出法による完全分割2012

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会第92春期年会
    • Place of Presentation
      東京
    • Year and Date
      2012-03-25
  • [Presentation] CIDT を伴う2-クロモンカルボン酸誘導体のジアステレオ選択的光二量化反2012

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会第92春期年会
    • Place of Presentation
      東京
    • Year and Date
      2012-03-25
  • [Presentation] ラセミ化優先晶出法によるラセミ体スクシンイミドの完全分割2012

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会第92春期年会
    • Place of Presentation
      東京
    • Year and Date
      2012-03-25
  • [Presentation] Photodimerization of Chromone Derivativ es and a New Methodology of Chiral In duction Using Preferential Crystallization with Photoracemization2011

    • Author(s)
      Masami Sakamoto
    • Organizer
      The 8th Korea-Japan Symposium on Frontier Photoscience
    • Place of Presentation
      Seoul, Korea
    • Year and Date
      2011-10-30
  • [Presentation] ラセミ化優先晶出法による環状イミドおよびアミドの完全分割2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      第20回有機結晶シンポジウム
    • Place of Presentation
      富山市
    • Year and Date
      2011-10-20
  • [Presentation] 鎖状イミドの形成するキラル結晶によるキラルメモリーの創製と不斉反応への応用2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      第20回有機結晶シンポジウム
    • Place of Presentation
      富山市
    • Year and Date
      2011-10-20
  • [Presentation] CIETを伴うクロモンカルボン酸誘導体のエナンチオ選択的な光二量化反応2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      第20回有機結晶シンポジウム
    • Place of Presentation
      富山市
    • Year and Date
      2011-10-20
  • [Presentation] 光ラセミ化優先晶出による不斉発現と増幅2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      2011年光化学討論会
    • Place of Presentation
      宮崎
    • Year and Date
      2011-09-08
  • [Presentation] ベンゾフェノン骨格を有する新規光配向剤の開発2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      2011年光化学討論会
    • Place of Presentation
      宮崎
    • Year and Date
      2011-09-08
  • [Presentation] クロモン誘導体の分子内[2+2]光環化付加反応2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      2011年光化学討論会
    • Place of Presentation
      宮崎
    • Year and Date
      2011-09-08
  • [Presentation] キラルなキノロンアミドとキラルな酸との塩形成による軸不斉の制御とキラルメモリーの創製2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      第61回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      千葉
    • Year and Date
      2011-05-22
  • [Presentation] 光ラセミ化優先晶出法による不斉の発現2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会春期年会
    • Place of Presentation
      神奈川
    • Year and Date
      2011-03-27
  • [Presentation] 芳香族アミドの可逆的不斉制御を利用した不斉反応への展開2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会春期年会
    • Place of Presentation
      神奈川
    • Year and Date
      2011-03-27
  • [Presentation] スクシンイミド及びイソインドリノン誘導体のラセミ化優先晶出法による不斉の発現と増幅2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会春期年会
    • Place of Presentation
      神奈川
    • Year and Date
      2011-03-27
  • [Presentation] アキラルなキノロンアミドの不斉結晶を利用したタンデム不斉反応2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会春期年会
    • Place of Presentation
      神奈川
    • Year and Date
      2011-03-27
  • [Presentation] クロモン誘導体の分子間および分子内[2+2]光環化付加反応2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会春期年会
    • Place of Presentation
      神奈川
    • Year and Date
      2011-03-27
  • [Presentation] CIST を伴うエナンチオ及びジアステレオ選択的光二量化反応2011

    • Author(s)
      坂本昌巳, 他
    • Organizer
      日本化学会春期年会
    • Place of Presentation
      神奈川
    • Year and Date
      2011-03-27
  • [Presentation] Photochemical asymmetric reaction in fluid media using the molecular chirality controlled by spontaneous crystallization2010

    • Author(s)
      Masami Sakamoto
    • Organizer
      Pacifichem
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2010-12-17
  • [Presentation] Photodimerization of Chromone Derivatives and a New Methodology of Chiral In duction Using Preferential Crystallization with Photoracemization2010

    • Author(s)
      Masami Sakamoto
    • Organizer
      Pacifichem
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2010-12-17
  • [Presentation] キノロンアミドのキラル結晶を用いたタンデム不斉反応2010

    • Author(s)
      坂本昌巳, 他
    • Organizer
      有機結晶シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2010-11-01
  • [Presentation] 環状アミド及びイミドのラセミ化優先晶出による不斉の発現と増幅2010

    • Author(s)
      坂本昌巳, 他
    • Organizer
      有機結晶シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2010-11-01
  • [Presentation] 光ラセミ化-優先晶出による不斉発現2010

    • Author(s)
      坂本昌巳, 他
    • Organizer
      有機結晶シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2010-11-01
  • [Presentation] キラルなキノロンアミドとキラルな酸との塩形成による軸不斉の制御とキラルメモリーの創製2010

    • Author(s)
      坂本昌巳, 他
    • Organizer
      第20回有機結晶シンポジウム
    • Place of Presentation
      富山市
    • Year and Date
      2010-10-20
  • [Presentation] 光二量化反応における不斉の自然発現と増幅2010

    • Author(s)
      坂本昌巳, 他
    • Organizer
      光化学討論会
    • Place of Presentation
      千葉市
    • Year and Date
      2010-09-08
  • [Presentation] キラルメモリー効果を利用したキノロンアミド誘導体のタンデム不斉反応2010

    • Author(s)
      坂本昌巳, 他
    • Organizer
      光化学討論会
    • Place of Presentation
      千葉市
    • Year and Date
      2010-09-08
  • [Presentation] クロモン誘導体と種々アルケンの分子間[2+2]光環化付加反応2010

    • Author(s)
      坂本昌巳, 他
    • Organizer
      光化学討論会
    • Place of Presentation
      千葉市
    • Year and Date
      2010-09-08
  • [Presentation] ジアステレオ選択的なクロモン誘導体の光二量化反応2010

    • Author(s)
      坂本昌巳
    • Organizer
      光化学討論会
    • Place of Presentation
      千葉市
    • Year and Date
      2010-09-08
  • [Presentation] 芳香属アミドの光と熱による可逆的エピマー化反応2010

    • Author(s)
      坂本昌巳, 他
    • Organizer
      光化学討論会
    • Place of Presentation
      千葉市
    • Year and Date
      2010-09-08
  • [Presentation] Chiral Induction Using Preferential Crystallization with Photodimerization and Photoracemization2010

    • Author(s)
      Masami Sakamoto
    • Organizer
      XXIII IUPAC Symposium on Photochemistry
    • Place of Presentation
      Ferrara, Italy
    • Year and Date
      2010-07-13
  • [Book] InCrystallization2012

    • Author(s)
      Masami Sakamoto, Takashi Mino
    • Total Pages
      59-80
    • Publisher
      Y. Mastai, InTech, ISBN
  • [Book] 光学活性医薬品開発とキラルプロセス化学技術2011

    • Author(s)
      坂本昌巳
    • Total Pages
      300-318
    • Publisher
      サイエンス & テクノロジー株式会社

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Published: 2013-07-31  

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