C-C bond cleavage of 2-acylimidazolium salts in a sequence involving a new ester homoenolate equivalent. A synthesis of γ-lactones
Abstract
Reaction of the anion of 2-(1-tri-isopropylsiloxyallyl)-N-methoxymethylimidazole with ketones and aldehydes proceeds regioselectivity to give the enol silyl ethers of 2-acylimidazoles which suffer cleavage to γ-lactones after desilylation, N-methylation, and base treatment.
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