Development of carbenoid chemistry and synthetic applications

2015 Fiscal Year Final Research Report

• Project/Area Number: 26860008
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Chiba University
• Principal Investigator: Harada Shingo 千葉大学, 薬学研究科(研究院), 助教 (50722691)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Keywords: アミド / 金属カルベノイド / 挿入反応 / ロジウム / 金 / ヘテロ環

Outline of Final Research Achievements

We developed a novel synthetic method for obtaining a wide variety of nitrogen-bridged bicyclic compounds with a catalytic process, Rh-catalyzed formal carbenoid insertion into an amide C-N bond. Using dirhodium tetrapivalamidate complex, various azabicycloalkane derivatives were obtained in good to excellent yield, successfully demonstrating the broad substrate scope of the developed process. A formal synthesis of anatoxin-a was accomplished by using rhodium-catalyzed formal amide insertion reaction. In addition, we successfully developed a diastereoselective synthetic method of functionalized quinolizidinone and indolizidinone derivatives from mixed N,O-acetals with a terminal alkyne unit and nucleophiles with two reactive sites using a gold (I)/Bronsted acid binary catalytic system.

Free Research Field

有機合成化学