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Stereoretentive Deuteration of ?-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 ?-carbon (70-99%). For ?-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

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Stereoretentive Deuteration of α-Chiral Amines with D<sub>2</sub>O.

Hale Lillian V A LVA Szymczak Nathaniel K NK

Journal of the American Chemical Society 20161006 41

We present the direct and stereoretentive deuteration of primary amines using Ru-bMepi (bMepi = 1,3-(6'-methyl-2'-pyridylimino)isoindolate) complexes and D<sub>2</sub>O. 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 exchang ...[more]

PMID: 27709928

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