A new route to 5- and 6-membered ring sultones

Abstract

Reaction of 1,2- or 1,3-alkanedisulfonate esters with one equivalent of n-butyllithium in tetrahydrofuran at −78 to 10° affords 5- and 6-membered ring sultones. Similar treatment of alkanesulfonate esters of 1,2-halohydrins gives 5-membered ring sultones. 1,2-Diols and 1,2-halohydrins of known stereochemistry were converted into 5-membered ring sultones in which the stereochemistry at 2 of the 3 ring carbon atoms is uniquely defined. Extension of these reactions to the formation of 7- and 8-membered ring sultones was not successful and products derived from an initial intermolecular reaction were obtained.