CONVENIENT SYNTHESES OF CHIRAL CYCLIC SULFINATES (SULTINES) FROM UNSATURATED ALCOHOLS

The reaction of unsaturated alcohols with N-sulfinyl-p-toluenesulfonam ide (TsNSO) is shown to lead stereoselectively to chiral cyclic or bic yclic sulfinates (sultines). The reactions occur at ambient temperatur es and afford a general route to delta- and epsilon-sultines which are notable for their crystallinity and thermal stability. These studies confirm the preservation of stereochemical integrity of the carbon ato m alpha to the oxygen atom in the sultine ring. Some unsaturated aldeh ydes furnish sultines via a tandem oxo-ene cyclization and subsequent ring closure to the sultine. In some reactions, N-toluenesulfonamide d erivatives of sultines (compounds of type 11) were isolated, and since those were converted into the sultines by the action of BF3-OEt(2), s uch sulfonamides are considered to be intermediates in the reaction pa thway.