A New Horner−Wadsworth−Emmons Type Coupling Reaction between Nonstabilized β-Hydroxy Phosphonates and Aldehydes or Ketones

2003/01/25 by John F. Reichwein, Brian L. Pagenkopf · 1 citation
Chemistry · #Organophosphorus compounds synthesis #Phosphorus compounds and reactions #Synthetic Organic Chemistry Methods

paper · doi:10.1021/ja027658s

openalex publication_date 2003/01/25 · openalex created_date 2019/06/27 · openalex updated_date 2026/06/26

Abstract

Treatment of nonstabilized beta-hydroxy phosphonic acid mono methyl esters with diisopropyl carbodiimide at ambient temperature leads to clean stereospecific elimination. The phosphonic acid mono alkyl esters are accessible by the selective partial saponification of dimethyl or diethyl alkyl phosphonates with NaOH or MgBr(2). Isolated yields over both hydrolysis and elimination steps average 55-75%.

Citations

• The Utility of Phosphonate Carbanions in Olefin Synthesis
• The Synthesis of Olefins from O,O'-Dialkyl β-Lithioalkylphosphonothioate Esters
• Olefin synthesis with organic phosphonate carbanions

Cited by

• Horner–Wadsworth–Emmons reaction [wikipedia]