Development of Enantioselective Acylation Based on Hydrogen-Bonding Strategy

2018 Fiscal Year Final Research Report

• Project/Area Number: 17K17903
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry; Organic chemistry
• Research Institution: Okayama University
• Principal Investigator: Mandai Hiroki 岡山大学, 自然科学研究科, 特任助教 (60534427)
• Project Period (FY): 2017-04-01 – 2019-03-31
• Keywords: 有機分子触媒 / 求核触媒 / アシル化 / エナンチオ選択的 / N,N-ジメチル-4-アミノピリジン / 1,3-ジオール / 糖

Outline of Final Research Achievements

With an optically active DMAP with tertiary alcohols moiety developed by our group, we examined enantioselective acylation of more complexed polyols. When the reaction was carried out using linear or cyclic 1,3-diol or 1,2,3-triol derivatives, the target monoacylated products were successfully obtained in high yield with high enantioselectivity. We also examined the regioselective acylation of carbohydrates for the synthesis of chiral building with high synthetic utility value. As a result of various control experiments, it was revealed that this reaction had high reaction acceleration effect and enantioselectivity (or regioselectivity) by hydrogen bonding.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究成果は，医薬品，農薬，天然物などの生物活性化合物合成に利用できるキラルビルディングを迅速かつ効率的に合成できる方法であり，医薬品や農薬などのファインケミカルの分野に大きく波及するものと期待している．