Desymmetrization of myo-inositol derivatives by lanthanide catalyzed phosphitylation with C2-symmetric phosphites

Duss, Michael; Capolicchio, Samanta; Linden, Anthony; Ahmed, Nisar; Jessen, Henning J

doi:10.1016/j.bmc.2015.03.023

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Duss, M., Capolicchio, S., Linden, A., Ahmed, N., & Jessen, H. J. (2015). Desymmetrization of myo-inositol derivatives by lanthanide catalyzed phosphitylation with C2-symmetric phosphites. Bioorganic & Medicinal Chemistry, 23(12), 2854–2861. https://doi.org/10.1016/j.bmc.2015.03.023

Abstract

Desymmetrization by phosphorylation represents a promising method with potential impact in many different areas of research. C2-Symmetric phosphoramidites have been used to desymmetrize myo-inosi- tol derivatives by functionalization at different positions. With this method, 1:1 mixtures of diastere- omers are obtained that can be separated subsequently. In this work, activation of a C2-symmetric phosphoramidite is achieved by addition of pentafluorophenol (PFP) and leads to a reactive PFP phos- phite, which can then be coupled to pro