A new synthetic approach to enantiomerically enriched dihydrobenzofurans: use of a hydrolytic kinetic resolution and an intramolecular epoxide ring opening protocol using 1-benzyloxy-2-oxiranylmethylbenzenes

A novel approach towards the preparation of racemic 1-benzyloxy-2-oxiranylmethylbenzenes using dimethyldioxirane and their hydrolytic kinetic resolution using (R,R)(Salen)Co(III)(OAc) (Jacobsen’s catalyst) to afford the (R)-epoxides and (S)-1,2-diols, enantioselectively, is described. The (R)-1-benzyloxy-2-oxiranylmethylbenzenes were then cyclized via an intramolecular epoxide opening reaction to give (S)-2-hydroxymethyl-2,3-dihydrobenzofurans.