Phosphate groups play a significant role in numerous biological systems, and are commonly found in a wide range of natural products, biological messengers, and pharmaceuticals. Fingolimod (code name FTY720) is an immunomodulating pro-drug used to treat multiple sclerosis, which is selectively phosphorylated <i>in-vivo</i> by sphingosine kinases to produce (S)-FTY720-phosphate, the active immunomodulating agent. We report a method for the enantioselective phosphorylation of a model compound for FTY720 using a BINOL-titanium catalyst. Reaction conditions screened include temperature, identity of base, identity of titanium ligands, and reagent ratios. To further elucidate a mechanism and determine a catalyst structure, nonlinear experiments were conducted and showed a positive nonlinear effect, suggesting a catalyst species oligomeric in BINOL.<br/>

Catalytic enantioselective phosphorylation of an FTY720 model diol

255th National Meeting (2018)

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