Abstract

Stannylcarbamate 1 proved to be a selective agent for generating organotin(IV) enolates from α-halo ketones. Thus, a Darzens reaction was achieved under mild and neutral conditions. The reaction took place without any side reactions and even with aliphatic α-halo ketones bearing enolizable α'-hydrogens. Various types of α,β-epoxyketones and esters were obtained in the one-pot reaction. The stereoselectivity of the reaction was influenced by changing the halogen substituent of the α-halo ketones and by additives

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