In the course of organic synthesis, particularly for multi-step synthesis or natural product total synthesis, the selection of appropriate protective groups for the intended functionality is crucial in order to achieve chemoselective synthetic goals. The development of many useful protective groups has been reported based on the functionality of the anilino group. Herein, we discuss our study of various protective groups and the processes we used to establish compatibility with anilino functionality via the implementation of Oxone-mediated oxidative esterification in methanol. The results and the details of our experiments are reported herein.
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