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

2019 Fiscal Year Final Research Report

• 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
• Keywords: 有機分子触媒 / 不斉合成 / アミノ酸

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.

Free Research Field

有機合成化学

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。