We present the direct and stereoretentive deuteration of primary amines using Ru-bMepi (bMepi = 1,3-(6'-methyl-2'-pyridylimino)isoindolate) complexes and DO. High deuterium incorporation occurs at the α-carbon (70-99%). For α-chiral amines, complete retention of stereochemistry is achieved when using an electron-deficient Ru catalyst. The retention of enantiomeric purity is attributed to a high binding affinity of an imine intermediate with ruthenium, as well as to a fast H/D exchange relative to ligand dissociation.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6578574 | PMC |
| http://dx.doi.org/10.1021/jacs.6b07879 | DOI Listing |
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