Development of chiral bis(halonium) salts as highly active and functionalized halogen-bonding catalyst

2023 Fiscal Year Final Research Report

• Project/Area Number: 22K14674
• 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: Chiba University
• Principal Investigator: Yoshida Yasushi 千葉大学, 大学院工学研究院, 准教授 (10773963)
• Project Period (FY): 2022-04-01 – 2024-03-31
• Keywords: 触媒的不斉合成 / ハロゲン結合 / キラルハロニウム塩 / Mannich反応

Outline of Final Research Achievements

In this research, the chiral bis(halonium) salts were synthesized and evaluated as highly active halogen-bonding catalyst. The chiral bis(iodonium) salt was selected as model bis(halonium) salt, and prepared from commercial BINAM (1,1'-Binaphthyl-2,2'-diamine) in several steps. The obtained salt was applied as chiral catalyst in Mannich reaction with bulky nucleophiles, which was in difficulty for getting high stereoselectivity with previous catalytic system. Our developed chiral catalyst worked well in this challenging reaction and the corresponding products were afforded in high stereoselectivities (up to 99% ee).

Free Research Field

触媒的不斉合成

Academic Significance and Societal Importance of the Research Achievements

本研究で開発されたキラルビスハロニウム塩触媒は，従来の触媒では困難であったかさ高い求核剤を用いるMannich反応に適用することで，高い立体選択性で対応する生成物の合成を可能とした。本成果は不斉触媒分野だけでなく，近年応用が期待されているハロゲン結合の応用としても興味深く，また本反応で得られた生成物群はキラルアミンという医薬品分子によく見られる骨格を有しているため，今後はその薬理活性分子としての応用にも期待される。