84224-37-3Relevant articles and documents
Preparation of Vinylsulfonates from Trimethylsilyl Enol Ethers - Synthetic Consequences of a Remarkable Cation Effect
Hirsch, Elisabeth,Huenig, Siegfried,Reissig, Hans-Ulrich
, p. 3687 - 3696 (2007/10/02)
The C/O-selectivity observed in the sulfonylation of the enolate ion 5 with benzenesulfonyl fluoride depends strongly on the nature of the gegenion.Li+ yields the β-oxosulfone 3 by C-sulfonylation exclusively.The fraction of O-sulfonylation is increased with the size of the cation, yielding the vinylsulfonates 6b exclusively in the presence of Cs+ or quaternary ammonium ions.From this behaviour a regio- and stereoselective synthesis of vinylsulfonates is developed starting from the corresponding trimethylsilyl enol ethers.