144667-65-2Relevant academic research and scientific papers
A Novel Darzens-Type Reaction Promoted by Tributylstannylcarbamate
Shibata, Ikuya,Yamasaki, Hayahide,Baba, Akio,Matsuda, Haruo
, p. 6909 - 6914 (2007/10/02)
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-epoxy ketones and esters were obtained in this one-pot reaction.The stereoselectivity of the reaction was influenced by changing the halogen substituent of the α-halo ketones and by additives.Moreover, the present method could be appliedto γ- and δ-halo ketones as enolate precursors, and five- and six-membered cyclic compounds were obtained.
