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 functionalit...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.展开更多
文摘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.
