Development of novel organocatalysts based on hydrogen-bond at benzyl position

2022 Fiscal Year Final Research Report

• Project/Area Number: 20K06948
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
• Research Institution: Tokyo University of Pharmacy and Life Science
• Principal Investigator: MIURA Tsuyoshi 東京薬科大学, 薬学部, 教授 (40297023)
• Project Period (FY): 2020-04-01 – 2023-03-31
• Keywords: 有機分子触媒 / 不斉反応 / 水素結合 / ベンジル位

Outline of Final Research Achievements

I developed novel N,N-dibenzyl diaminomethylenemalononitrile (DMM) organocatalysts. Dibenzyl DMM catalysts achieved highest stereoselectivity for asymmetric conjugate additions of aldehydes to vinyl sulfones. The dibenzyl DMM catalysts efficiently promoted Henry reactions of trifluoromethyl enones, which has never been reported, to successfully afford 1,2-adducts with excellent stereoselectivity. Moreover, the asymmetric 5-exo selective bromolactonization of stilbene-type carboxylic acids, which has never been reported, could be achieved using dibenzyl DMM catalyst.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

申請者が開発したジベンジル型ジアミノメチレンマロノニトリル(DMM)触媒は既存の有機分子触媒では観察されない触媒活性を示した。ジベンジル型DMM触媒を用いることによって，これまで高立体選択的に合成できなかったキラル化合物を高い光学純度で合成することに成功した。今後，合成に成功したキラル分子が様々な医薬品合成に活用されると予想されるため，学術的にも社会的にも意義ある研究成果である。