Development of Asymmetric Transfer Hydrogenation with a Bifunctional Oxo-Tethered Ruthenium Catalyst in Flow for the Synthesis of a Ceramide (D-erythro-CER[NDS])
The development of an efficient synthetic route for an optically active ceramide compound (d-erythro-CER[NDS]) is described. The route proceeds through asymmetric transfer hydrogenation in a pipes-in-series flow reactor with oxo-tethered ruthenium complex-catalyzed dynamic kinetic resolution. This synthesis was accomplished without any expensive reagents, and none of the intermediates required isolation. This resulted in a robust process that has been successfully run on a production scale.
Dynamic kinetic resolution: An efficient route to anti α-amino- β-hydroxy esters via Ru-SYNPHOS catalyzed hydrogenation
The Ru(II)-catalyzed hydrogenation of α-amino-β-keto esters as their hydrochloride salts affords preparation of the corresponding anti α-amino-β-hydroxy esters under mild conditions with high diastereoselectivities and enantioselectivities via dynamic kinetic resolution.
A versatile route to syn- and anti-α-amino β-hydroxy esters from β-keto esters by dynamic kinetic resolution with Ru-SYNPHOS catalyst
A general and practical synthesis of both syn- and anti-α-amino β-hydroxy esters with high levels of selectivity by the use of Ru-SYNPHOS catalysts is reported. The key transformations include asymmetric hydrogenations of α-N-substituted β-keto esters pro