The chemistry of phosphonamide stabilized allylic carbanions derived from the 1,2-addition of tervalent phosphorus siloxanes with α,β-unsaturated aldehydes has been studied. An in situ synthesis of allylic α-silyloxyphosphonamides, followed by metalation and regioselective γ-alkylation of the allylic carbanion, yields a versatile “active ester”. Transesterification under mild conditions gives esters and lactones and defines a new homoenolate equivalency.
ASJC Scopus subject areas
- Colloid and Surface Chemistry