Development of acid-base hybrid organocatalysts and their application to unprecedented organic synthesis

2022 Fiscal Year Final Research Report

• Project/Area Number: 18H01975
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: Tokyo University of Agriculture and Technology (2020-2022); Kyoto University (2018-2019)
• Principal Investigator: Kano Taichi 東京農工大学, 工学(系)研究科(研究院), 教授 (40372560)
• Project Period (FY): 2018-04-01 – 2022-03-31
• Keywords: 有機触媒 / 有機酸触媒 / 有機塩基触媒 / アミン触媒 / 不斉合成

Outline of Final Research Achievements

In this study, we have developed acid-base hybrid organocatalysts that have both acidic and basic functional groups. A number of organocatalysts with both acidic and basic functional groups including amino acids have been reported. However, when acidic and basic functional groups coexist, they form acid-base complexes to inactivate the catalyst. We have developed novel catalysts by introducing both acidic and basic functional groups into a rigid framework to suppress the formation of intramolecular acid-base complexes. These acid-base hybrid organocatalysts showed sufficient reactivity and were found to be effective for novel asymmetric reactions.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究では、高い活性や選択性を示す酸塩基複合触媒を設計するためには、その酸性官能基と塩基性官能基の双方が接触しないよう、剛直な基本構造上に配置することが重要であることが明らかとなった。従来は触媒の土台となる剛直な基本構造としてビナフチル化合物が汎用されていたが、原料の調達やその修飾は容易ではなかった。本研究ではそれに代わる新しい基本構造を見出し、その簡便な合成法も確立した。本研究は、今後の触媒設計の際の新たな指針となり得る。