Sulfoxide-directed desymmetrisation of cyclohexa-1,4-dienes

Cyclohexa-2,5-dien-1-ylmethanol derivatives have been subjected to a short sequence featuring esterification to introduce a malonate side-chain, oxidation of the doubly allylic position and stereoselective cyclisation. When used in conjunction with a chiral sulfoxide, the cyclisation is diastereoselective (2:1) favouring one of the diastereotopic double-bonds.