Stereoselective synthesis of β-substituted α,β-unsaturated esters by dialkylcuprate coupling to the enol phosphate of β-keto esters

Abstract

The anions from β-keto esters or β-diketones were reacted with diethyl phosphorochloridate to yield the corresponding enol phosphates. These enol phosphates were coupled with dialkylcuprates to produce the β-substituted α,β-unsaturated esters or ketones in good yield. Starting from acyclic β-keto esters this sequence was used to stereoselectively generate tri- and tetrasubstituted olefins.