Catalytic asymmetric synthesis of chiral oxa-heterohelicenes based on dynamic kinetic resolution

2014 Fiscal Year Final Research Report

• Project/Area Number: 24550059
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kumamoto University
• Principal Investigator: IRIE Ryo 熊本大学, 自然科学研究科, 教授 (70243889)
• Co-Investigator(Renkei-kenkyūsha): IMAHORI Tatsushi 熊本大学, 大学院先導機構, 特任助教 (90433515)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: ヘテロヘリセン / ラセン不斉 / 複素芳香族化合物 / π共役系化合物 / 環化芳香族化 / パラジウム触媒 / 酸素酸化 / 環化異性化

Outline of Final Research Achievements

Helicenes and heterohelicenes are well-known as helically twisted compounds like a pattern of snail. Thus, helicenes are chiral and the development of catalytic asymmetric synthesis of their right-handed and left-handed isomers is a very important subject in the research field of organic synthetic chemistry and materials science. Against to this background, we have tried to develop unprecedented catalytic asymmetric synthesis of novel heterohelicenes in the present study. In consequent, we found some new "domino" cyclization reactions, in which multiple bonds are formed one after another in one pot literally like "dominoes". These results should be very promising to provide new methods for the synthesis of a variety of heterohelicenes, which are otherwise difficult to synthesize.

Free Research Field

有機合成化学