Deuterated compounds are of significant interest in academia for mechanistic studies, and to the pharmaceutical industry for improving pharmacokinetics of known drugs. For these applications, controlling site-selectivity and stereoselectivity must be considered in the development of H-D exchange catalysts. Chiral compounds are a particularly challenging target as current H-D exchange methods often result in racemic mixtures. This poster will describe the development of H-D exchange reactions, including enantioselective deuterium incorporation into α-chiral amines, using amide-derived N,N,N-Ru(II) complexes previously reported by our group. Achiral primary amines, alcohols, and aromatic substrates are also shown to undergo H-D exchange using D2O as the deuterium source. A late stage modification of the N,N,N-pincer ligand resulted in complete retention of stereochemistry of 1-phenylethylamine with 90% deuterium incorporation. The origin of enantioselectivity will be assessed through catalyst and substrate modifications. Additionally, the application of this method to biologically relevant substrates will be addressed.

Development of enantioselective H-D exchange reactions by Ru-[NNN] pincer complexes

252nd National Meeting (2016)

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