The use of diazabicyclo[2.2.2]octane as a novel highly selective dechloroacetylation reagent

Abstract

In a study directed toward the use of the chloroacetyl protecting group in carbohydrate synthesis, the sterically hindered tertiary amine diazabicyclo[2.2.2]octane (DABCO) was found to give complete and selective cleavage of the chloroacetyl group in the presence of other ester functions such as benzoyl and acetyl groups at primary and/or secondary positions.