Thiolanes chiral

Figure 20.3 Development of chiral thiolanes with a locked conformation.

C-chiral racemic y-hydroxy sulfides were also resolved using PEL under kinetic resolution conditions. The products were transformed into optically active 3-(alkanesulfonyloxy)thiolane salts (Scheme 1). Similarly, 1,2-cyclic sulfite glycerol derivatives cis and trans) were resolved into enantiomers via a Pseudomonas cepacia-catalysed acylation with vinyl butyrate. The E values depended on the solvent used and varied from 2 to 26. ... 

Subsequently, Paquette and Johnson used LAH reductions to convert strained thietane or thiolane derivatives to their respective sulphides, generally in good yields. Whitney and Cram described the LAH reduction of a chiral derivative of benzothiophene sulphone, as outlined in equation (24). The authors also noted the formation of hydrogen gas and suggested that their results were consistent with those of Bordwell as outlined in equation (22), namely that reduction takes place by the formation of an aluminium oxide and hydrogen gas. In this case, the reduction clearly cannot involve the formation of an a-sulphonyl carbanion and it is unlikely that any C—S bond cleavage and reformation could have occurred. 

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