Protecting groups often play an essential role in
organic synthesis, particularly for multi-step synthesis or natural product total synthesis.
Various protecting groups areavailable to mask the vulnerable functionality; phenolic
hydroxy groups are noteworthy examples,but their stability differs when protected. Herein,
the compatibility of protective phenolic functionality was investigated with
the implementation of indium(III)
triflate-catalyzed oxidative esterification using Oxone in methanol. A wide
range of protective moieties was selected and subjected to Oxone-mediated
oxidative esterification. For example, sulfonates were found to be sufficiently
stable and inert whereas acetals were susceptible to reaction conditions. The
details of this investigation are provided.
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