The Journal of organic chemistry

A practical synthesis of 3-acyl cyclobutanones by [2+ 2] annulation. Mechanism and utility of the Zn (II)-catalyzed condensation of α-chloroenamines with electron- …

JM O'Brien, JS Kingsbury

Index: O'Brien, Jeannette M.; Kingsbury, Jason S. Journal of Organic Chemistry, 2011 , vol. 76, # 6 p. 1662 - 1672

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Citation Number: 15

Abstract

New conditions for the conversion of simple tertiary amides to α-chloroenamines and their use in Zn (II)-catalyzed cycloaddition reactions with commercial α, β-unsaturated carbonyl compounds allows rapid, regiocontrolled access to 3-acyl cyclobutanones. Reactions take place at ambient temperature without solvent, giving strained [2+ 2] adducts with all-carbon- substituted quaternary carbon atoms. Ab initio calculations of the putative keteniminium ...