Substitution of the acetoxy groups of dialkoxymethylacetates by organometallic reagents: a route to allyl-, propargyl-, homoallyl-, homopropargyl- and α-stannylacetals

Article abstract of DOI:10.1016/0022-328X(92)83085-V

The substitution of the acetoxy groups of dialkoxymethylacetates by organometallic reagents has been examined in a search for new methods of preparing functional acetals.The efficiency of the substitution of the acetoxy group is highly dependent on the nature of the organometallic reagents: soft nucleophiles with strong electrophilic assistance by the counterion are the best reagents.Allyl-, propargyl-, homoallyl-, homopropargyl- and α-stannylacetals have been made by this route, in which dialkoxymethylacetates often function as useful substitutes for dialkylphenylorthoformates.