Stereoretentive Deuteration of α-Chiral Amines with D₂O.

ABSTRACT: We present the direct and stereoretentive deuteration of primary amines using Ru-bMepi (bMepi = 1,3-(6'-methyl-2'-pyridylimino)isoindolate) complexes and D₂O. 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.

SUBMITTER: Hale LVA 

PROVIDER: S-EPMC6578574 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature