A new Horner-Wadsworth-Emmons type coupling reaction between nonstabilized beta-hydroxy phosphonates and aldehydes or ketones.
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%.
Reichwein
John F
JF
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
Pagenkopf
Brian L
BL