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Development of hydrogen bond-donating asymmetric Lewis acid catalyst for control of multiple selectivities

Research Project

Project/Area Number 17H07164
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionRikkyo University

Principal Investigator

TSUTSUMI Ryosuke  立教大学, 理学部, 助教 (90801697)

Project Period (FY) 2017-08-25 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2018: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords有機合成化学 / 不斉合成 / ルイス酸
Outline of Final Research Achievements

In the course of investigating the simultaneous control of regio- and stereoselectivity using hydrogen bond-donating chiral Lewis acids, we found that the reaction between γ-butenolide and α-ketoester proceeded at the α-position of γ-butenolide in the presence of bifunctional organobase catalyst. We newly designed a chiral 2,2'-bipyridine-type ligand with a side chain bearing urea functional group as a hydrogen bond donor. This hydrogen bond-donating chiral Lewis acid was found to catalyze various stereoselective reactions.

Academic Significance and Societal Importance of the Research Achievements

化合物が持つ本質的な性質に左右されない位置選択性、あるいは触媒制御による位置異性体の作り分けが実現できれば、既存の方法では実現できない新しい有機化合物の合成法の立案につなげられる可能性がある。今回、ルイス酸と水素結合との協同効果によりこれを達成するべく、新規不斉配位子を設計・開発した。本研究成果は、反応基質が持つ複数の反応点を識別可能な配位子設計へと発展させるための端緒となる。

Report

(3 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Annual Research Report
  • Research Products

    (3 results)

All 2019

All Presentation (3 results)

  • [Presentation] キラルジアミンとアキラル色素で構成される水素結合錯体の円二色性(CD)及び円偏光発光(CPL)特性2019

    • Author(s)
      磯貝拓、神作八起、堤亮祐、山中正浩
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 亜鉛ビスアミジナート触媒によるα-ケトエステル・亜リン酸ジエステル・アルデヒドの三成分連結型不斉付加反応の開発2019

    • Author(s)
      高徳知朗、堤亮祐、山中正浩
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 金属ビスアミジン触媒によるβ,γ-不飽和α-ケトエステルとインドールの不斉Friedel-Crafts反応2019

    • Author(s)
      長谷部智紀、堤亮祐、山中正浩
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report

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Published: 2017-08-25   Modified: 2020-03-30  

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