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

Abstract

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.