Fluoride-Mediated Reactions of Enol Silyl Ethers. Regiospecific Monoalkylation of Ketones

Article abstract of DOI:10.1021/ja00368a018

Treatment of enol silyl ethers with alkyl halides in the presence of benzyltrimethylammonium fluoride and molecular sieves at room temperature gives the corresponding monoalkylated products with high regiospecificity.In most cases no polyalkylated products formed in the reaction.The alkylation reaction is highly chemospecific: esters, epoxides, and even ketones survive the reaction conditions.The reactions of various cyclohexanone derivatives proceed with the preferential axial attack of the electrophile.