期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 138, 期 41, 页码 13489-13492出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b07879
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资金
- NIH [GM 111486]
We present the direct and stereoretentive deuteration of primary amines using Ru-bMepi (bMepi = 1,3-(6'-methy1-2'-pyridylimino) isoindolate) complexes and D2O. High deuterium incorporation occurs at the alpha-carbon (70-99%). For a-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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