Development of Novel Chiral Nucleophilic Catalyst Possessing Triazadiphosphole Structure and Its Application to Enantioselective Acylation

2015 Fiscal Year Final Research Report

• Project/Area Number: 25810057
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Tohoku University
• Principal Investigator: Kondoh Azusa 東北大学, 理学(系)研究科(研究院), 助教 (30645544)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: 有機分子触媒 / トリアザジホスホール / 不斉有機塩基触媒 / 二官能性触媒

Outline of Final Research Achievements

With the aim of developing a novel nucleophilic catalyst possessing both of a stereogenic center and a hydrogen-bond donor cite at the position adjacent to the nucleophilic cite, a 1,2,4-triazadiphosphole catalyst was designed and investigated. As a result, we achieved the short-step construction of the triazadiphosphole framework. The catalytic activity of the triazadiphosphole thus synthesized was evaluated, and the compound was found to function as an organobase although the application as a nucleophilic catalystwas not succeeded. After the revision of catalyst structure, a novel bifunctional chiral strong organobase catalyst, which has a quaternary ammonium moiety as a hydrogen-bond donor, was designed and synthesized. The application of the catalyst to some reactions suggested that the quaternary ammonium moiety could effectively serve as a hydrogen-bond donor and involve the stereocontrol of the reactions.

Free Research Field

有機合成化学