1- aminophosphonate

Stereoselective hydrolysis of racemic l-(//-phenylacetylamino) alkanephos-phonic acids performed in the presence of penicillin acylase under the kinetic resolution conditions gave both the unreacted substrates and the products - the corresponding 1-aminophosphonic acids in high yields and with full enantioselec-tivity. The unreacted A -acyl derivatives were hydrolysed chemically and in this way each enantiomer of the free acid was obtained (Scheme 5). ... 

Keywords aldehyde, diethyl phosphite, alumina/ammonium formate, microwave irradiation, 1 -aminophosphonate... 

Phosphono analogues 206 of glutathione have been prepared as inhibitors of glutathione 5-transferases. 1-Aminophosphonate structures have potential as haptens in a number of areas and examples of such compounds reported include 207 and 208. The A-hydroxy-l-aminophosphonates 208 were prepared from... 

Schrader, T., and Steglich, W., Phosphorus analogs of amino acids. Part 4. Syntheses of unusual 1-aminophosphonic acids via Diels-Alder reactions of diethyl (7V-acyliminomethyl)phosphonates, Synthesis, 1153, 1990. 

Defacqz, N., Touillaux, R., Cordi, A., and Marchand-Brynaert, J., (1-Aminophosphonic compounds derived from methyl l-dimethoxy-phosphoryl-2-succinimidocyclohex-3-ene-l-carboxylates, J. Chem. Soc., Perkin Trans. 1, 2632, 2001. 

B. Kaboudin, M. Sorbium, j8-Cyclodextrin as an efficient catalyst for the one-pot synthesis of 1-aminophosphonic esters in water. Tetrahedron Lett., 2007, 48, 9015-9017. 

PhenyIethylamine has been resolved following conversion into diastereoiso-meric glycosylamines by reaction with 1,2,3,4,6-penta-O-acetyl-D-glucopyranose. iV-Ribofuranosyl derivatives of nitrogen-containing heterocyclic compounds are referred to in Chapter 21, and the conversion of Schiff-base derivatives of aldehydo-sugais into 1-aminophosphonates is noted in Chapter 18. 

Miscellaneous Reactions. A one-pot three components synthesis of a variety of primary 1-aminophosphonates was reported using Al(OTf)3 as a catalyst (eq 11). Relative to other Lewis acids, Al(OTf)3 generally offered the best reaction times and yields using various aldehydes. The reaction was also possible using various primary amines in the same conditions. ... 

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