Stereospecific internal almylation of terminal γ,δ-epoxy acrylates

Article abstract of DOI:10.1016/S0040-4039(97)00635-7

The alkylation of ethyl (S)- and (R)-4,5-epoxy-2-pentenoates (11) and (12), chiral terminal γ,δ-epoxy acrylates prepared from D-mannitol, by trialkylaluminum in the presence of water occurs rcgioselectively at the γ position, i.e., at the internal position, to yield a sole product respectively with net inversion of configuration. The method provides useful chiral synthons for natural product synthesis.