Stereoselective construction of quaterary stereogenic center

2015 Fiscal Year Final Research Report

• Project/Area Number: 25410113
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Toyohashi University of Technology
• Principal Investigator: SHIBATOMI Kazutaka 豊橋技術科学大学, 工学(系)研究科(研究院), 准教授 (00378259)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: 不斉合成 / ハロゲン化合物 / SN2反応 / 二型糖尿病治療薬 / 第三級アルコール / フェノキシド / 不斉触媒 / キラルルイス酸

Outline of Final Research Achievements

Asymmetric synthesis of chiral organic molecules is a highly useful synthetic method for the preparation of various functional molecules. In particular, development of flexible methods for the preparation of compounds with a chiral quaternary stereogenic center is strongly required in medicinal chemistry. Previously, we succeeded in the enantioselective chlorination of b-keto esters with newly developed chiral Lewis acid catalyst. Here, we found that the SN2 reactions of resulting chlorides afforded the corresponding substituted products without loss of enantiopurity with water or phenol as the nucleophile. Furthermore, we demonstrated that the resulting substituted products could be converted into potential candidates of anti-diabetic drug.

Free Research Field

有機合成化学