A novel phosphorus-carbon bond formation by ring opening with diethyl phosphite of oxazolines derived from serine |
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Authors: | Franck Meyer Anna Maria Papini Sylvain Jugé |
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Institution: | a Université de Cergy Pontoise, UMR CNRS 8123, 5 mail Gay Lussac 95031 Cergy Pontoise, France b Dip. di Chimica Organica, Univ. degli Studi di Firenze, via della Lastruccia 13, 50019 Sesto Fiorentino (FI), Italy c Université de Bourgogne, LSEO UMR CNRS 5188, 6 boulevard Gabriel, 21000 Dijon, France |
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Abstract: | A new reaction of oxazolines derived from serine with diethyl phosphite leading to ring opening products with P-C bond formation is reported. This reaction, which proceeds under neutral conditions and without the use of any halogenated intermediate, results in a mixture of racemic α- and β-phosphono alanines in an approximate 1:2 ratio, with isolated yields up to 77%. The mechanism involves the rearrangement of the oxazoline into the corresponding α-benzamido acrylate, followed by addition of the diethyl phosphite to the double bond. Since no significant transesterification is observed, this method constitutes a simple route for α- and β-phosphono amino acids bearing suitable protecting groups. |
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Keywords: | Amino acids and derivatives Phosphonic acids and derivatives Oxazolines |
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