Alkenylphosphonic acids synthesis

Ohler, E., and Kotzinger, S., Thermal reanangement of trichloroacetimidic esters of allylic a-hydroxyphosphonates. A convenient way to (3-amino-1-alkenylphosphonic acids, Synthesis, 497, 1993. 

Hamden, M.R., Parkin, A., Parratt, M.J., and Perkins, R.M., Novel acyclonucleotides. Synthesis and antiviral activity of alkenylphosphonic acid derivatives of purines and a pyrimidine, J. Med. Chem., 36, 1343, 1993. 

E. Synthesis of Alkenylphosphonic Acids Using the Wittig Reaction... 

In 2013, the synthesis of phosphaisocoumarins is achieved by Miura and coworkers via Rh(III)-catalyzed oxidative annulation of phenylphosphonic acids with alkynes (Scheme 6.25a) [40]. Shortly after, Lee and coworkers reported a similar result using phenylphosphinic or alkenylphosphonic acids to afford phosphaisocoumarins in good yields (Scheme 6.25b) [41]. 

Scheme 11 indicates the usefulness of salts derived from Wittig ylide reagents and anhydrides of perfluorocarboxylic acids in the synthesis of fluorinated alkenylphosphonic diesters (127), often together with (epoxyalkyl)phosphonic diesters (128)(Rf = CF3 or... 

The addition of a nitroalkane to an alkenylphosphonic diester is exemplified by the interaction of nitromethane with diethyl ethenylphosphonate in the presence of NaOEt, when the product is diethyl (3-nitropropyl)phosphonate and by a similar addition to 1,1-bis(diethoxyphosphinoyl)ethane . In the initial stages of a synthesis of (4,5,6-trihydroxy-3-oxohexyl)phosphonic acid, the nitro sugar 76 was made to add to dibenzyl ethenylphosphonate, but the resultant (3-nitropropyl)phosphonic dibenzyl ester 77 was then used without isolation. ... 

Hayashi T, Senda T, Takaya Y, Ogasawara M (1999) Rhodium-Catalyzed asymmetric 1,4-addition to 1-alkenylphosphonates. J Am Chem Soc 121 11591-11592 Giordano C, Castaldi G (1989) First asymmetric synthesis of enantiomerically pure (1R,2S)-(-)-(l,2-Epoxypropyl)phosphonic acid (Fosfomycin). J Org Chem 54 1470-1473... 

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