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

Abstract

Upon treatment with base, the diethyl vinyl phosphate derivatives of five-, six-, and seven-membered-ring lactones undergo rearrangement to a-phosphono lactones in very good yields. Because the vinyl phosphates can be prepared in situ, these a-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 a-phosphono esters, but yields are generally lower and the rearrangement becomes minimal with esters hindered at the β-position. © 1989, American Chemical Society. All rights reserved.