Development of an amine-Lewis acid co-catalytic system as multifunctional catalysts

2017 Fiscal Year Final Research Report

• Project/Area Number: 25708016
• Research Category: Grant-in-Aid for Young Scientists (A)
• Allocation Type: Partial Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Kyoto University
• Principal Investigator: Kano Taichi 京都大学, 理学研究科, 准教授 (40372560)
• Project Period (FY): 2013-04-01 – 2018-03-31
• Keywords: 有機分子触媒

Outline of Final Research Achievements

Enolizable aldehydes can be utilized as nucleophiles by converting to enamines, and various amine-catalyzed reactions including Mannich reaction with imines have been developed to date. In the present study, carbamates such as BocNH2 was found to be applicable as a novel organocatalyst to activate aldehydes. It was found that the Mannich-type reaction between Boc-protected aminals and aldehydes proceeds in the presence of a phosphoric acid catalyst. Since less basic carbamates do not deactivate the strong Bronsted acid catalyst, carbamate-Bronsted acid cocatalyst system would be applicable to the reactions using less reactive electrophiles. The asymmetric variant of the present Mannich-type reaction through dual activation of aldehydes and aminals has also been demonstrated with a chiral phosphoric acid catalyst.

Free Research Field

有機合成化学