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Preparation of optically active ketones from equilibrium systems using highly selective chiral molecular recognition.

Research Project

Project/Area Number 26460027
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionTokushima Bunri University

Principal Investigator

KAKU HIROTO  徳島文理大学, 薬学部, 准教授 (90299339)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2016: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2015: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2014: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Keywords平衡複雑系 / 不斉分子認識 / デラセミ化 / ホスト-ゲスト化学 / TADDOL型ホスト分子 / ジアステレオ制御 / 包接錯体 / 光学活性化合物
Outline of Final Research Achievements

trans-cis mixture of (5R)-2-benzyl-5-methylcyclohexanone were converted to cis-form (91% de) by a thermodynamic equilibrium condition using TADDOL-type host molecule 1 in alkaline aqueous MeOH. The efficiency of this conversion was strongly influenced by the ratio of the solvent components (H2O/MeOH). Cyclohexenone was converted to (S)-3-methoxycyclohexanone using TADDOL-type host molecule 1 and DBU as a basic catalyst in H2O/MeOH (3:7). X-ray analytical studies were also carried out and disclosed the nature of this chiral molecular recognition process in the solid phase.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (9 results)

All 2016 2015 Other

All Presentation (7 results) (of which Invited: 1 results) Remarks (2 results)

  • [Presentation] 熱力学的平衡条件下での光学活性シクロペンタノン類の調製2016

    • Author(s)
      井藤美浪,加来裕人,上原李佳子,谷由紀子,堀川美津代,角田鉄人
    • Organizer
      第21回プロセス化学会東四国フォーラムセミナー
    • Place of Presentation
      徳島
    • Year and Date
      2016-10-22
    • Related Report
      2016 Annual Research Report
  • [Presentation] 熱力学的平衡条件下での光学活性シクロペンタノン類の調製2016

    • Author(s)
      加来裕人,井藤美浪,上原李佳子,谷由紀子,堀川美津代,角田鉄人
    • Organizer
      有機合成化学協会中国四国支部第74回パネル討論会:次世代を切り拓く全合成研究の若い力
    • Place of Presentation
      徳島
    • Year and Date
      2016-10-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] 熱力学的平衡条件下での光学活性置換シクロペンタノン類の調製2016

    • Author(s)
      加来裕人,井藤美浪,上原李佳子,谷由紀子,堀川美津代,角田鉄人
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-28
    • Related Report
      2015 Research-status Report
  • [Presentation] 不斉結晶場における平衡条件下での分子認識現象 -ラセミ混合物を光学活性体にする新手法-2016

    • Author(s)
      加来裕人
    • Organizer
      第19回プロセス化学会東四国フォーラムセミナー
    • Place of Presentation
      徳島
    • Year and Date
      2016-01-09
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] α-モノ置換シクロペンタノンの不斉分子認識2015

    • Author(s)
      井藤美浪,加来裕人,堀川美津代,角田鉄人
    • Organizer
      第54回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会
    • Place of Presentation
      高知
    • Year and Date
      2015-10-31
    • Related Report
      2015 Research-status Report
  • [Presentation] 包接錯体化を利用した平衡複雑系からの光学活性ケトン類の調製2015

    • Author(s)
      加来裕人,谷由紀子,上原李佳子,新垣友梨,堀川美津代,角田鉄人
    • Organizer
      第107回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2015-06-09
    • Related Report
      2015 Research-status Report 2014 Research-status Report
  • [Presentation] ノルボルナン誘導体光学活性ホスト分子を用いたエナンチオ選択的な液膜移送2015

    • Author(s)
      加来裕人,櫻間大次朗,大津留更,七條友哉,清水雅子,小村沙耶馨,堀川美津代,角田鉄人
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Remarks] 徳島文理大学薬学部薬品化学研究室ホームページ

    • URL

      http://p.bunri-u.ac.jp/lab03/HINKA/HOME.html

    • Related Report
      2015 Research-status Report 2014 Research-status Report
  • [Remarks] 徳島文理大学薬学部薬品化学研究室ホームページ(英語版)

    • URL

      http://p.bunri-u.ac.jp/english/?p=379

    • Related Report
      2015 Research-status Report 2014 Research-status Report

URL: 

Published: 2014-04-04   Modified: 2018-03-22  

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