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Development of catalytic incorporation of an oxygen atom into organic substrates from atmospheric molecular oxygen.

Research Project

Project/Area Number 15K18837
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionKitasato University

Principal Investigator

YAMAMOTO DAISUKE  北里大学, 薬学部, 助教 (10509970)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords酸素分子 / 触媒反応 / マンガン錯体 / オキシム / ヒドロキシアミン / 酸化反応 / ジヒドロイソオキサゾール環 / 不斉反応
Outline of Final Research Achievements

Developing a new methodology for transition metal-catalyzed oxidation reactions has been extensively studied in the recent decade, and molecular oxygen is essentially recognized as an ideal oxidant. Despite developing several elegant oxidation processes involving molecular oxygen as a sole oxidant, methodologies for directly incorporating molecular oxygen into organic substrates remain a major challenge in synthetic chemistry. Based on such backgrounds, we have found that manganese(III) acetylacetonate is a highly efficient catalyst (generally 0.02-0.5 mol%, and a minimum of 0.001 mol%) for the oxidative cyclization reactions of unsaturated oximes to provide 4,5-dihydroisoxazoline alcohols, and the hydroperoxidation reactions of carbon-carbon double bond of enynes as well as styrene derivatives using N-hydroxyphthalimide, N-hydroxybenzotriazole or N-hydroxysuccinimide through the direct incorporation of molecular oxygen present in air (open flask).

Report

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

    (13 results)

All 2017 2016 2015

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 2 results) Presentation (10 results)

  • [Journal Article] Synthesis of sialic acid derivatives based on chiral substrate-controlled stereoselective aldol reactions using pyruvic acid oxabicyclo[2.2.2]octyl orthoester2017

    • Author(s)
      Norimura, Y.; Yamamoto, D.; Makino, K.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 15 Issue: 3 Pages: 640-648

    • DOI

      10.1039/c6ob02412b

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Manganese-catalysed hydroperoxidation of carbon-carbon double bonds using molecular oxygen present in air and hydroxylamine under ambient conditions2016

    • Author(s)
      Yamamoto, D.; Soga, M.; Ansai, H.; Makino, K.
    • Journal Title

      Org. Chem. Front.

      Volume: 3 Issue: 11 Pages: 1420-1424

    • DOI

      10.1039/c6qo00318d

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Manganese-Promoted Oxidative Cyclization of Unsaturated Oximes Using Molecular Oxygen in Air under Ambient Conditions2016

    • Author(s)
      Yamamoto, D.; Oguro, T.; Tashiro, Y.; Soga, M.; Miyashita, K.; Aso, Y.; Makino, K.
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2016 Issue: 31 Pages: 5216-5219

    • DOI

      10.1002/ejoc.201600998

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] マンガン錯体による空気中の酸素分子を酸素源としたヒドロキシアミン類の付加を伴う過酸化物合成法の開発2017

    • Author(s)
      山本大介、曽我誠之、安齋広将、牧野一石
    • Organizer
      日本薬学会 第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Annual Research Report
  • [Presentation] 空気中の酸素分子を利用したマンガン錯体によるβ-ヒドロペルオキシ-N-アルコキシフタルイミドの合成2016

    • Author(s)
      山本大介、曽我誠之、安齋広将、牧野一石
    • Organizer
      第42回 反応と合成の進歩シンポジウム
    • Place of Presentation
      静岡
    • Year and Date
      2016-11-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] アルドール反応を基軸としたシアル酸及び誘導体の合成研究2016

    • Author(s)
      法村勇佑、山本大介、牧野一石
    • Organizer
      日本薬学会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 空気中の酸素分子を利用したマンガン触媒によるジヒドロイソオキサゾール環構築法の開発2015

    • Author(s)
      山本大介、小黒卓人、田代裕樹、曽我誠之、牧野一石
    • Organizer
      反応と合成の進歩シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2015-10-26
    • Related Report
      2015 Research-status Report
  • [Presentation] アルドール反応を基軸としたシアル酸及び誘導体の合成研究2015

    • Author(s)
      法村勇佑、山本大介、牧野一石
    • Organizer
      GlycoTOKYO
    • Place of Presentation
      神奈川
    • Year and Date
      2015-10-24
    • Related Report
      2015 Research-status Report
  • [Presentation] アルドール反応を基軸としたシアル酸及び誘導体の合成研究2015

    • Author(s)
      法村勇佑、山本大介、牧野一石
    • Organizer
      北里化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2015-09-26
    • Related Report
      2015 Research-status Report
  • [Presentation] チイルラジカルを用いた触媒的連続環化反応の開発2015

    • Author(s)
      島田貴大、山本大介、牧野一石
    • Organizer
      北里化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2015-09-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 光学活性含硫黄化合物の合成とヒドロシリル化反応への応用2015

    • Author(s)
      千葉祐毅、山本大介、牧野一石
    • Organizer
      北里化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2015-09-26
    • Related Report
      2015 Research-status Report
  • [Presentation] マンガン触媒による空気中の酸素分子固定化を伴うジヒドロイソオキサゾール環構築法の開発2015

    • Author(s)
      山本大介、小黒卓人、宮下和仁、麻生芳明、牧野一石
    • Organizer
      有機合成化学セミナー
    • Place of Presentation
      神奈川
    • Year and Date
      2015-09-15
    • Related Report
      2015 Research-status Report
  • [Presentation] アルドール反応を基軸としたシアル酸及び誘導体の合成研究2015

    • Author(s)
      法村勇佑、山本大介、牧野一石
    • Organizer
      日本薬学会 関東支部大会
    • Place of Presentation
      千葉
    • Year and Date
      2015-09-12
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2018-03-22  

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