Synthesis of α-Phosphono Lactones and Esters through a Vinyl Phosphate-Phosphonate Rearrangement

Article abstract of DOI:10.1021/jo00281a012

Upon treatment with base, the diethyl vinyl phosphate derivatives of five-, six-, and seven-membered-ring lactones undergo rearrangement to α-phosphono lactones in very good yields.Because the vinyl phosphates can be prepared in situ, these α-phosphono lactones can be obtained from the parent lactones in a one-flask protocol, making this methodology a convenient alternative to the traditional Arbuzov synthesis.An analogous reaction sequence can be used to prepare some α-phosphono esters, but yields are generally lower and the rearrangement becomes minimal with esters hindered at the β-position.