Literature DB >> 27709928

Stereoretentive Deuteration of α-Chiral Amines with D2O.

Lillian V A Hale1, Nathaniel K Szymczak1.   

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.

Entities:  

Year:  2016        PMID： 27709928      PMCID： PMC6578574          DOI： 10.1021/jacs.6b07879

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  22 in total

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  17 in total

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7.  Controllable deuteration of halogenated compounds by photocatalytic D2O splitting.

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9.  Mild, Selective Ru-Catalyzed Deuteration Using D2 O as a Deuterium Source.

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10.  Semiconductor photocatalysis to engineering deuterated N-alkyl pharmaceuticals enabled by synergistic activation of water and alkanols.

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