1,3-Dioxonium cation facilitated Ritter-type reaction: facile synthesis of protected aminopolyols

A unique 1,3-dioxonium cation facilitated Ritter-type reaction was discovered when glycerol dipivaloates were treated with strong acid in acetonitrile. The stereoselectivity and regioselectivity of this new Ritter-type reaction were further explored by using erythritol tripivaloate and 1,2,4-butanetriol dipivaloate as the substrates. Several protected aminopolyols were generated as important chiral building blocks. This reaction was employed to synthesize a protected aminosugar lactone.