Thiocarbonyl compounds Thio-Claisen rearrangement

Some applications of the thio-Claisen rearrangement to the syntheses of thiocarbonyl compounds, particularly unsaturated dithiocstcrs and thionesters, and of its stereocontrol aspects are reviewed in [120]. A particularly high stereoselectivity was observed with S-allyl derivatives of P-hydroxydithioesters syn products were obtained exclusively, according to the accompanying scheme [495,496]. 

Base-induced S-allylation of dithioesters [17,18], thionoselenoesters [19] as well as tertiary thioamides [20-23] with allylic halides and alcohols [24] have been commonly used to generate S-allyl ketene-S,W-acetals (W = S,Se, N), which are prone for a thio-Claisen rearrangement. In fact, the marked trend of the starting thiocarbonyl compounds to render the cis-... 

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