Development of a catalytic method for radical generation at alpha-position of carboxylic acid

2020 Fiscal Year Final Research Report

• Project/Area Number: 18K14207
• Research Category: Grant-in-Aid for Early-Career Scientists
• Allocation Type: Multi-year Fund
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: Hokkaido University
• Principal Investigator: Shimizu Yohei 北海道大学, 理学研究院, 准教授 (60609816)
• Project Period (FY): 2018-04-01 – 2021-03-31
• Keywords: カルボン酸 / ホウ素触媒 / 光

Outline of Final Research Achievements

In this research project, we were able to achieve the following two results: (1) discovery of boron-catalyzed α-allylation of carboxylic acids in combination with visible light irradiation, and (2) development of boron-catalyzed α-amination of carboxylic acids. In the first achievement, we were able to discover a new reactivity of boron catalysis, and it will be the basis for expanding the application to more diverse reaction systems. In the second achievement, we established a method for synthesizing sterically hindered α-amino acids , which is difficult to synthesize by other methods. This method would accelerate the application of unnatural amino acids to various field by supplying order-made amino acids.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

カルボン酸のα位アリル化反応の開発においては、ホウ素触媒と光照射を組み合わせることで、これまでにない反応性を見出すことができたという点で学術的意義が大きい。一方、カルボン酸α位アミノ化反応の開発は、非天然αアミノ酸の簡便な供給方法として利用可能である。非天然アミノ酸は医薬化合物をはじめとして利用価値が高いため、入手容易なカルボン酸から付加価値の高いアミノ酸を合成できるという点で社会的意義があると言える。