Tetrahedron p. 10315 - 10326 (1992)
Update date:2022-09-26
Topics:
Desert, Stephane
Metzner, Patrick
Ramdani, Mohamed
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 deg 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.
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