Tetrahedron

A new practical synthesis of silyl enol ethers: Part. I. From simple aldehydes and ketones

…, F Duboudin, F Moulines, O Babot, J Dunogues

Index: Cazeau, P.; Duboudin, F.; Moulines, F.; Babot, O.; Dunogues, J. Tetrahedron, 1987 , vol. 43, # 9 p. 2075 - 2088

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Citation Number: 167

Abstract

A new, practical route to enoxysilanes is described from simple enolizable aldehydes or ketones, using the trimethylchlorosilane-sodium iodide—tertiary amine reagent in acetonitrile. From certain aldehydes, an onium intermediate has been isolated. A conformational study of this onium intermediate and a thermal unimolecular syn-elimination process may explain the stereoselectivity of the reaction. Such an interpretation can be ...