A calcium-catalyzed approach to accessing α-functionalized amines via deacetylation has been developed. Using Ca(NTf2)2/nBuNPF6 as a mild Lewis acid system, a range of α-acetoxy substrates undergo smooth deacetylation and functionalization. The reaction displays excellent substrate tolerance and accommodates diverse nucleophiles, including sulfur, indole, amide, and cyanide derivatives. Furthermore, telescoped deprotection-reprotection protocols enable facile access to a variety of N-protected amines in high yields, providing a simple and practical route to valuable α-functionalized amine scaffolds.
Cameron et al. (Mon,) studied this question.