New Generation in Deuterium Chemistry: Development of Novel Deuterated Organocatalysts and Biologically Interesting Molecules

2016 Fiscal Year Final Research Report

• Project/Area Number: 15K13644
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Kochi University
• Principal Investigator: Kotsuki Hiyoshizo 高知大学, 学内共同利用施設等, 特任教授 (80093954)
• Co-Investigator(Renkei-kenkyūsha): ICHIKAWA Yoshiyasu 高知大学, 教育研究部自然科学系, 教授 (60193439) ; NAKANO Keiji 高知大学, 教育研究部自然科学系, 准教授 (50399747)
• Project Period (FY): 2015-04-01 – 2017-03-31
• Keywords: 有機分子触媒 / 重水素化有機触媒 / 生体機能性分子 / チオ尿素触媒 / 重水素化

Outline of Final Research Achievements

The purpose of this project has been focused on the development of a new selective method for deuteration of organocatalysts and biologically interesting molecules. As a result, we could succeed in synthesizing new deuterated thiourea organocatalysts for the use in novel synthetic reactions. For example, we found that a catalytic system composed of trityl halide and thiourea catalyst could serve as novel organo-based Lewis acids for the use in carbonyl-ene cyclization. In addition, we also found that the asymmetric Michael addition reaction of alpha-substituted cyclic ketones was efficiently promoted by primary amine-based organocatalysts under high pressure conditions. Finally, we could also succeed in obtaining a new approach to introduce deuterium atoms into the biologically interesting molecules. We believe that these results will give important information for other chemists who work in this important field.

Free Research Field

有機合成化学