Enantioselective reduction of esters: synthesis of optically active α-acetoxy ethers

An enantioselective reduction and acetylation of esters to α-acetoxy ethers is described. Reduction with a NaAlH4–ephedrine reagent followed by in situ acetylation gives 2 with good enantiomeric excess. This reaction is limited in scope, but it demonstrates that enantioselective reductions of esters are possible.