Tetrahedron Letters
Volume 42, Issue 52, 24 December 2001, Pages 9221-9223
A new procedure for the synthesis of silyl enol ethers from S-
-silylbenzyl thioesters without need for either bases or catalysts via C---C bond formation is described. Solutions of S--silylbenzyl thioesters were simply heated at 180°C for 24 h in a sealed tube to give silyl enol ethers in good yields with high stereoselectivity. Cyclization of the dipoles generated by thermal rearrangement of the silyl group and elimination of sulfur afforded silyl enol ethers.
The method represents a new preparative method of silyl enol ethers under completely neutral conditions with no need for any catalyst or additives.
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