An Efficient Synthesis of β,γ -Disubstituted α -Diethoxyphosphoryl-γ -lactones: A Convenient Approach to α -Methylene-γ -lactones

Abstract

A synthesis of β,γ -disubstituted α -diethoxyphosphoryl-γ -lactones from easily available dicyclohexylammonium 3-aryl-2-diethoxyphosphoryl-4-oxopentanoates is reported. The phosphonolactones were transformed into the corresponding α -methylene-γ -lactones by means of the Horner–Wadsworth–Emmons reaction with formaldehyde.

Keywords:

• α-Alkylidene-γ-lactones
• α-diethoxyphosphoryl-γ-lactones
• Horner–Wadsworth–Emmons reaction

Dedicated to Professor Marian Mikołajczyk from the CBMiM PAN in Łódź, Poland, on the occasion of his 70th birthday.

This work was financed by the Ministry of Education and Science (Project No. 3 T09A 075 28).