Activated Glycerol Carbonates, Versatile Reagents with Aliphatic Amines: Formation and Reactivity of Glycidyl Carbamates and Trialkylamines

The reactivity of mesylated and tosylated glycerol carbonate towards secondary and tertiary amines has been studied, and allowed regioselective access to carbamates which could then be transformed into glycidylcarbamates. By tuning the reaction conditions, we were able to direct the reaction towards the synthesis of novel 5-aminomethyldioxolan-2-ones derivatives. The opening of glycidylcarbamates with various amines was also explored, and showed the opportunity to use glycerol as a linker between two different amines moieties.