Efficient Synthesis of Enantiomerically Pure Amines by Highly Active Species

2014 Fiscal Year Final Research Report

• Project/Area Number: 25870458
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry; Chemical pharmacy
• Research Institution: Okayama University
• Principal Investigator: MANDAI Hiroki 岡山大学, 自然科学研究科, 助教 (60534427)
• Project Period (FY): 2013-04-01 – 2015-03-31
• Keywords: 光学活性アミン / 速度論的光学分割 / キラルブレンステッド酸 / 対アニオン制御型反応

Outline of Final Research Achievements

We have interested in the development of the conceptually new approach for the kinetic resolution of amines. Especially reactions based on asymmetric counteranion-directed catalysis with chiral Brønsted acid are very attractive. We hypothesized that the chiral ion pairs derived from a chiral phosphate anion and achiral acylpyridinium salts should be good reactive species in enantioselective acylation of amines. We screened pyridine derivatives, solvents, and amount of reagents. As a result of this screening, the reaction system gave the product in 20% conversion with 82 : 18 er (s = 5.3).

Free Research Field

有機合成化学