Kinetic resolution of racemic alkoxy oxiranes by chiral lithium amides

The isomerization of alkoxy oxiranes with chiral lithium amides has been carefully investigated with the aim of finding an enantioselective approach to hydroxy enol ethers. Thus, the stereoselectivities and enantiomeric excesses for ring opening of cis- or trans-2,3-epoxy-1-methoxymethoxyoctane in presence of chiral lithium amides are reported.