摘要

New conditions for the conversion of simple tertiary amides to alpha-chloroenamines and their use in Zn(II)-catalyzed cycloaddition reactions with commercial alpha,beta-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 intermediate and studies with styrenyl olefins suggest a dual role for Zn(OTf)(2) during catalysis.

  • 出版日期2011-3-18