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Abstract
The Claisen rearrangement of precursors bearing a stereogenic centre adjacent to carbon 1 of the pericyclic nucleus has been investigated in the sulfur series. Dithioesters having a methyl and various alkyl or alkenyls groups on the β-carbon were deprotonated by LDA. The resulting enethiolates were allylated on sulfur to give S-allyl ketenedithioacetals. The thio-Claisen transposition of the latter compounds was achieved either at room temperature or at 101°C to afford good yield of allylated dithioesters. Diastereomeric selectivities up to 95 : 5 have been observed. These results have been explained by a steric effect and correlated to allylic strain values.
Published Version
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