Development of novel allylmetal generation method and its application

2014 Fiscal Year Final Research Report

• Project/Area Number: 25860004
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: The University of Tokyo
• Principal Investigator: SHIMIZU Yohei 東京大学, 薬学研究科(研究院), 助教 (60609816)
• Project Period (FY): 2013-04-01 – 2015-03-31
• Keywords: アリル銅 / 不斉触媒 / インドール / アレン / アリル化

Outline of Final Research Achievements

We developed a novel method to generate allylcopper species from an allenylanilide, which possesses both an allene moiety and an aniline moiety in one molecule. Cu(I) catalyst facilitates a generation of allylcopper species along with formation of indole structure. The generated allylcopper species can work as nucleophile to various carbonyl compounds including ketones.
The reaction proceeded in enantioselective manner by utilizing a chiral diphosphine ligand. Thus the reaction produced chiral 2-(2-hydroxyethyl)indoles efficiently, whose scaffold is difficult to construct by other means.
The developed method is unique in simultaneous construction of indole structure and elongation of carbon scaffold.

Free Research Field

有機化学