Yb(OTf)₃‑Catalyzed Desymmetrization of <i>myo</i>-Inositol 1,3,5-Orthoformate and Its Application in the Synthesis of Chiral Inositol Phosphates

A variety of inositol phosphates including <i>myo</i>-inositol 1,4,5-trisphosphate, which is a secondary messenger in transmembrane signaling, were selectively synthesized via Yb­(OTf)₃-catalyzed desymmetrization of <i>myo</i>-inositol 1,3,5-orthoformate using a proline-based chiral anhydride as an acylation precursor. The investigated catalytic system could regioselectively differentiate the enantiotopic hydroxy groups of <i>myo</i>-inositol 1,3,5-orthoformate in the presence of a chiral auxiliary. This key step to generate a suitably protected chiral <i>myo</i>-inositol derivatives is described here as a unified approach to access inositol phosphates