Chiral polymer of cinchona alkaloid - peptide hybrid catalyst

2017 Fiscal Year Final Research Report

• Project/Area Number: 15K05517
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Polymer chemistry
• Research Institution: Toyohashi University of Technology
• Principal Investigator: Itsuno Shinichi 豊橋技術科学大学, 工学(系)研究科(研究院), 教授 (50158755)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: キラル高分子 / シンコナアルカロイド / スルホンアミド / スクアラミド / シンコナーペプチドハイブリッド / 有機分子触媒

Outline of Final Research Achievements

Cinchona alkaloid-peptide hybrid catalysts were established. Chiral squaramidess containing aminated cinchona alkaloid and peptide were prepared. These hybrid catalysts showed high level of stereoselectivities in asymmetric Michael reactions. Cinchona alkaloids contain vinyl group in their molecules. When iodophenyl group was introduced onto the hybrid catalyst, Heck coupling reaction occurred between the hybrid catalyst molecules to form chiral polymers. This is the first synthesis of chiral cinchona squaramide polymer. The polymeric chiral squaramides were used as catalysts in various asymmetric synthesis and showed excellent catalytic performances. In some cases, the polymeric catalysts showed higher stereoselectivity compared to the corresponding low-molecular hybrid catalysts. Since the polymeric catalysts we have developed are insoluble in commonly used organic solvents, the polymeric catalysts were easily recovered and reused many times.

Free Research Field

キラル高分子触媒