Dephosphonylation of β-Carbonyl Phosphonates

Abstract

A new methodology has been developed for the P−C bond cleavage of β-carbonyl phosphonates. The α,α-disubstituted β-keto phosphonates and the α-carbamoyl phosphonates have been shown to undergo dephosphonylation by reaction of their lithium enolate with LiAlH 4, followed by quenching with aqueous H 2 SO 4, affording regioselectively α,α-disubstituted ketone and α-substituted and α,α-disubstituted secondary amides.