Experimental Selection of SEM-Cl: From O/N-SEM Protection and Directed Functionalization of N-Heterocycles to the Introduction of Protected C1 Fragments

2-(Trimethylsilyl)ethoxymethyl chloride, abbreviated as SEM-Cl, was initially introduced into organic synthesis as a hydroxyl-protecting reagent. Subsequent studies showed that the utility of SEM-Cl is not limited to the construction of O-SEM protecting groups. It can also be used for nitrogen ...