Lewis acid-catalyzed phosphinoylation and halogenation of α,β-unsaturated ketones: access to γ-halo allylic phosphonates

Abstract

A Lewis acid-catalyzed phosphinoylation and halogenation of α,β-unsaturated ketones to synthesize γ-halo allylic phosphonates is described. This transformation consists of a phospha-Michael addition, unimolecular elimination dehydration cascade reaction for the introduction of versatile groups (–P(O)R₃R₄ and –X) in the resulting γ-substituted allylic phosphonates with high regio- and stereoselectivity.