Innovative Organocatalysis in Cooperation with Wood Nanocellulose and Amino Acids

2015 Fiscal Year Final Research Report

• Project/Area Number: 26660145
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Wood science
• Research Institution: Kyushu University
• Principal Investigator: KITAOKA Takuya 九州大学, (連合)農学研究科(研究院), 教授 (90304766)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Keywords: ナノセルロース / プロリン / 有機分子触媒 / アルドール反応 / カルボキシ基 / マトリックス効果 / 不斉合成 / 界面反応

Outline of Final Research Achievements

Catalysts accelerate various chemical reactions with high selectivity. In recent, “organocatalysts” have attracted much attention in chemistry, instead of rare metals and enzymes. Proline is well known as a first organocatalyst to catalyze an asymmetric aldol reaction; however it involves many difficulties in practical applications. Herein, we propose the interfacial aldol synthesis by the combination of proline and TEMPO-oxidized cellulose nanofibers. The aldol reaction of 4-nitrobenzaldehyde and acetone proceeded stoichiometrically and enantioselectively to synthesize (4R)-4-hydroxy-4-(4-nitrophenyl)-2-butanone. Proline alone showed very low catalytic efficiency and provided only racemic products. Thus, the cooperative interactions of catalysts and substrates on the crystalline nanocellulose must be a critical factor to enhance such asymmetric aldol reaction. Our challenge in pairing nanocellulose with organocatalysts will provide a new insight to interfacial asymmetric synthesis.

Free Research Field

木質科学・多糖材料化学