Development of Practical Synthetic Methods for Asymmetric Construction of Quaternary Carbon Atoms Using Simple Amino Acids as Catalysts

Research Project

Project/Area Number	17K05872
Research Category	Grant-in-Aid for Scientific Research (C)
Allocation Type	Multi-year Fund
Section	一般
Research Field	Synthetic chemistry
Research Institution	Asahikawa National College of Technology
Principal Investigator	YOSHIDA Masanori 旭川工業高等専門学校, 一般理数科, 准教授 (30322829)
Project Period (FY)	2017-04-01 – 2020-03-31
Project Status	Completed (Fiscal Year 2019)
Budget Amount *help	¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000) Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000) Fiscal Year 2018: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000) Fiscal Year 2017: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords	有機分子触媒 / 不斉合成 / アミノ酸 / 有機合成化学
Outline of Final Research Achievements	Asymmetric construction of quaternary carbon stereogenic centers is frequentry required in the the development of pharmaceuticals. To develop a practical method, it is important that the target compounds can be obtained in good yields with high enantioselectivity by a cost effective and environmet-friendly procedure. In this study, the author investigated the reaction of alpha-branched carbonyl compounds with alkyl halides by using a simple primary amino acid as an asymmetric organic catalyst for constructing a quaternary carbon stereogenic center at the neighboring carbon aton of the carbonyl group. By studying the reaction conditions thoroughly, the author succeeded to develop a method for the high enantioselective and high yielding alpha-alkylation of alpha-branched aldehydes.
Academic Significance and Societal Importance of the Research Achievements	本研究により，高度に立体が制御された不斉四級炭素を持つアルデヒドを収率良く得ることに成功した。この反応は触媒の入手や取り扱いが容易であり，また，従来法よりも環境負荷が小さくできるStorkエナミン－アルキル化反応であることも考えると，工業的な利用も視野に入れた実用性に優れた不斉四級炭素の構築法であるといえる。今後，本研究が医薬品に活用される生理活性物質などの合成法の開発に結びつくものと期待している。