Development of spirocyclic phosphoramidite-based hybrid diphosphorus ligands for enantioselective iridium-catalyzed hydrogenation of imines?

Organic & Biomolecular Chemistry Pub Date: 2022-10-21 DOI: 10.1039/D2OB01801B

Abstract

Unsymmetrical hybrid chiral diphosphorus ligands bearing a spirocyclic phosphoramidite scaffold have been developed and successfully applied in the iridium-catalyzed asymmetric hydrogenation of imines. With this newly developed chiral iridium catalytic system, a wide range of imines including sterically hindered ones could be hydrogenated to give the corresponding optically active amines in high yields (up to >99%) and with excellent enantioselectivities (up to >99% ee). The utility of this hydrogenation has been demonstrated by the preparation of the chiral fungicide (S)-benalaxyl.

Graphical abstract: Development of spirocyclic phosphoramidite-based hybrid diphosphorus ligands for enantioselective iridium-catalyzed hydrogenation of imines
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