Issue 6, 2017

Iridium-catalyzed asymmetric hydrogenation of cyclic iminium salts

Abstract

An enantioselective hydrogenation of cyclic iminium salts has been successfully realized by employing [Ir(COD)Cl]2 and chiral diphosphine ligands as catalyst, furnishing chiral N-alkyl tetrahydroisoquinolines and N-alkyl tetrahydro-β-carbolines with up to 96% ee and 88% ee, respectively. The hydrogenation provides a direct, simple and efficient protocol toward chiral tertiary amines. Meanwhile, asymmetric hydrogenation at the gram scale was also conducted smoothly without loss of reactivity and enantioselectivity.

Graphical abstract: Iridium-catalyzed asymmetric hydrogenation of cyclic iminium salts

Supplementary files

Article information

Article type
Research Article
Submitted
22 jan 2017
Accepted
23 feb 2017
First published
24 feb 2017

Org. Chem. Front., 2017,4, 1125-1129

Iridium-catalyzed asymmetric hydrogenation of cyclic iminium salts

Y. Ji, G. Feng, M. Chen, L. Shi, H. Du and Y. Zhou, Org. Chem. Front., 2017, 4, 1125 DOI: 10.1039/C7QO00060J

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