Diastereoselective synthesis of α-dicarbonyl cyclopropanes via a lanthanide amide-catalysed reaction

Abstract

Lanthanide bis(trimethylsilyl)amides, [(Me₃Si)₂N]₃Ln(μ-Cl)Li(THF)₃, were used as efficient catalysts for a one-pot reaction of α-ketoesters, dialkyl phosphite, and activated alkenes to produce α-dicarbonyl cyclopropanes in moderate to high yields. The reaction was stereoselective and the two adjacent carbonyls linked to the cyclopropane were in the cis-configuration. The high efficiency of the lanthanide amide in catalysing the reaction is the result of the cooperation between the lanthanide metal centre and the N(SiMe₃)₂ anion.