The synthesis of P-chiral amino acid-derived phosphonamidic anhydrides |
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Authors: | Sprott K T Hanson P R |
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Institution: | Department of Chemistry, University of Kansas, Lawrence, 66045-2506, USA. |
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Abstract: | The synthesis of an array of P-chiral amino acid-derived phosphonamidic anhydrides is described. These anhydrides are prepared by condensation of allylated amino acids 19-22 with methyl- or vinylphosphonic dichlorides 23 or 24 to produce three diastereomeric anhydrides 4-11a-c in good to excellent yields. The mechanistic issues concerning anhydride formation are discussed and supported by experimental results. Vinylphosphonamidic anhydrides 8-11 are further derivatized via the ring-closing metathesis (RCM) reaction to yield amino acid-derived bicyclic phosphonamidic anhydrides. |
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