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J Am Chem Soc. 2016 Oct 19;138(41):13489-13492. doi: 10.1021/jacs.6b07879. Epub 2016 Oct 6.

Stereoretentive Deuteration of α-Chiral Amines with D2O.

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1
Department of Chemistry, University of Michigan , Ann Arbor, Michigan 48109, United States.

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.

PMID:
27709928
DOI:
10.1021/jacs.6b07879

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