The synthesis of P-chiral amino acid-derived phosphonamidic anhydrides.
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.
Sprott
K T
KT
Department of Chemistry, University of Kansas, Lawrence, 66045-2506, USA.
Hanson
P R
PR
D000812:Anhydrides / Q000138:chemical synthesis* / Q000737:chemistry; D001862:Bone Resorption / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000812:Anhydrides; D063065:Organophosphonates; D010756:Phosphoric Acids