Development of direct nucleophilic addition to inert amides

2014 Fiscal Year Final Research Report

• Project/Area Number: 24750045
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Keio University
• Principal Investigator: SATO TAKAAKI 慶應義塾大学, 理工学部, 講師 (70509926)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: 有機化学 / 有機反応化学 / 天然物化学 / アミド / 求核付加反応 / 官能基選択性

Outline of Final Research Achievements

Amide functional groups are found in a wide variety of organic molecules including pharmaceuticals and functional materials. Therefore, efficient synthesis of amide bonds has been extensively studied. On the other hand, transformation of the generated amide groups is less explored than their construction.
In this study, we developed direct nucleophilic addition to amide groups using unique properties of a zirconium reagent. The developed method enabled installation of two functional groups in a single reaction. The most conspicuous feature of our method is the high chemoselectivity. The reaction proceeded in the presence of a variety of sensitive functional groups such as esters. The reaction was successfully applied to the total syntheses of biologically active alkaloids.

Free Research Field

化学