Highly Efficient Darzens Reactions Mediated by Phosphazene Bases under Mild Conditions

The highly basic and poorly nucleophilic phosphazene base P(1) -t-Bu promotes the Darzens condensation of α-halo esters with aromatic aldehydes affording α,β-epoxy esters in nearly quantitative yields under mild conditions and in short reaction times. The more basic P(4) -t-Bu phosphazene was found useful with low reactivity aldehydes. These reactions can be performed in aprotic organic solvents of low polarity, thus minimizing the hydrolysis of α,β-epoxy esters which often accompanies the base-promoted Darzens condensations.