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.
We present the direct ann class="Chemical">d stereoretentive deuteration of primaryamines using Ru-bMepi (bMepi = 1,3-(6'-methyl-2'-pyridylimino)isoindolate) complexes andD2O. 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 liganddissociation.
Authors: Emre M Isin; Charles S Elmore; Göran N Nilsson; Richard A Thompson; Lars Weidolf Journal: Chem Res Toxicol Date: 2012-02-28 Impact factor: 3.739