Regio-and Stereoselective Synthesis of Silyl Enol Ethers Using a New Base Electrogenerated from Hexamethyldisilazane

…, C Biran, P Cazeau, J Dunogues

Index: Bonafoux, Dominique; Bordeau, Michel; Biran, Claude; Cazeau, Philippe; Dunogues, Jacques Journal of Organic Chemistry, 1996 , vol. 61, # 16 p. 5532 - 5536

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Citation Number: 37

Abstract

The hexamethyldisilazane magnesium salt, a new base readily electrogenerated in an undivided cell fitted with a sacrificial magnesium anode, using a normally equilibrating medium (DME/15% vol HMPA mixture), exhibited a surprising regioselectivity leading to the less highly substituted silyl enol ethers from unsymmetrical ketones. This regioselectivity was not temperature dependent, but was strongly dependent on the nature and ...