Tetrahedron letters

Selective O-acylation of silyl enol ethers with acid halides mediated by a copper (I) salt

H Ito, T Ishizuka, J Tateiwa, A Hosomi

Index: Ito, Hajime; Ishizuka, Tomoko; Tateiwa, Jun-Ichi; Hosomi, Akira Tetrahedron Letters, 1998 , vol. 39, # 35 p. 6295 - 6298

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Citation Number: 10

Abstract

A new selective synthetic method of enol esters (O-acylated products) from silyl enol ether and acid chloride in the presence of CuCl is described. This reaction proceeds smoothly in DMI (1, 3-dimethyl-2-imidazolidinone) but not in a less polar solvent. The silicon-copper exchange reaction pathway is proposed for this transformation as in the cases of hydrosilane and alkynylsilane which were previously reported.