Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 23, Issue 4, Pages 452-461Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.8b00338
Keywords
asymmetric transfer hydrogenation; oxo-tethered ruthenium catalyst; dynamic kinetic resolution; pipes-in-series flow reactor; ceramide; DENEB
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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.
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