Development of Methodology for Construction of Cyclic Skeletons Using NHC-Catalyzed Umpolung-Type Gamma-Addition Reaction

2017 Fiscal Year Final Research Report

• Project/Area Number: 15K18841
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Chiba University
• Principal Investigator: Kuwano Satoru 千葉大学, 大学院理学研究院, 特任助教 (50733531)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: 含窒素複素環式カルベン / 炭素環構築反応 / 極性転換 / シクロペンテン誘導体 / 転位反応 / ハロゲン結合 / インドール誘導体 / 不斉合成

Outline of Final Research Achievements

The cyclic skeleton is a component included in many biologically active compounds, and the development of a novel methodology for construction of cyclic skeletons is an important research topic leading to the creation of medicines, agricultural chemicals and the like. In this research, we aimed to develop a new method for the synthesis of carbocycles using N-heterocyclic carbene (NHC)-catalyzed umpolung-type γ addition reaction. As a result of various investigations, the γ addition reaction promoted by the addition of NHC proceeded and succeeded in the synthesis of the multiply substituted cyclopentene derivative. We also found that various indole derivatives can be synthesized by using halogen bond donating type iodine catalyst induced by iodination of NHC in the process of this investigation.

Free Research Field

有機合成化学