Amines are ubiquitous in nature and are found in amino acids, the building blocks of the cells molecular machinery. Strategies for imine reduction is highly researched topic in the field of organic chemistry.  Here we propose to study the use of Lewis acid catalysts to form chiral amines, which have applications for the synthesis of pharmaceuticals and biologically relevant molecules, as well as potential uses in the context of materials, such as sensors. The goal of this research proposal is to investigate the use of carbocation catalysts such as triphenylcarbenium tetrafluoroborate in forming a chiral amine. The triphenylcarbenium acts as Lewis acid, binding to the nitrogen of the imine activating it for reduction with a hydride from Hanztch ester forming a chiral center. The catalyst is then released producing a chiral amine and an oxidized Hanztch pyridine.<br/>The preliminary results suggest that the reaction proceeds by Lewis acid carbocation catalysis. The most efficient carbocation so far is triphenylcarbenium tetrafluoroborate. The reaction with the highest yield in the presence of the proton sponge was achieved using trityl tetrafluoroborate as the carbocation (TR1, Figure 1), DCE as the solvent at 82 °C. This reaction was able to yield 72% of amine (table 1). The purpose of the proton sponge (2,6-Di-tert-butyl-4-methylpyridine) is to prevent catalysis of the imine by any potential adventitious Brønsted acid formed during the reaction. In the future, we will investigate the use of various imines and hydride sources to optimize the yield of reaction. Additionally, we will investigate the use of carbocations that contain a counterion in order to produce enantioenriched amines.<br/>

Lewis acid carbocation catalyzed reduction of imines

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.