Alkenylphosphonates: unexpected products from reactions of methyl 2-[(diethoxyphosphoryl)methyl]benzoate under Horner–Wadsworth–Emmons conditions

Abstract

Methyl 2-[(diethoxyphosphoryl)methyl]benzoate reacts with several aldehydes to produce an alkenylphosphonate as the major product, together with varying amounts of the expected Horner-Wadsworth-Emmons product, a 1,2-disubstituted E-alkene. Use of a bulky aldehyde or the tert-butyl ester favours the normal HWE product.

A novel, rapid and green method of phosphorylation under ultrasound irradiation and catalyst free conditions

“…Amidophosponates have received considerable attention from organic chemists, [1][2][3] they are considered as an important class of compounds, with several interesting biological activities. Their applications are signicant in agriculture as plant regulators, herbicides, 4 pesticides and in medicine as anticancer agents, 5 enzyme inhibitors, 6 peptide mimics, 7 antibiotics and pharmacological agents.…”

Rhodium-Catalyzed Enantioselective Hydrogenation of Unsaturated Phosphonates by ClickFerrophos Ligands

“…Chiral phosphonic acids and phosphonates are expected to be useful as chiral building blocks of optically active alkenes through the Horner–Wadsworth–Emmons reaction . They are also of biological interest; for example, chiral α- or β-hydroxy phosphonates and α- or β-amino phosphonates can be applied to antibacterial agents, enzyme inhibitors, and intermediates in biosynthetic processes .…”