Synthese von Aminosäurephosphanen und Darstellung von Derivaten des Triphenylphosphans durch palladiumkatalysierte P-C- Kupplung

摘要

The first section of this work was dedicated to the development of nucleophilic phosphination reactionson aromatic fluoro compounds. Phosphino- derivatives of the α-aminoacids phenylglycine and phenylalanine have been obtained by reaction of the potassium- salts of 2, or4-fluorophenylglycine- or alanine respectively with KPPh using DME as solvent. The x-raystructural analysis of reveals the bulky nature of the PPh- substituent in position to the amino acid substituent and the betaine type structure in theα-amino acid moiety of . Derivatives of2-diphenylphosphino-phenylglycine bearing N-, O-, P- protecting groups have been synthesed andinvestigated. N-acetyl protected amino acid was accessible by reaction of withAcO in good yields. The methylester was obtained by using equimolar amountsof HC(OMe)/ CFCOOH/ MeOH. Due to the low solubility of in solventslike toluene its reaction with sulphur failed, the phosphine oxide was easily accessible byoxidation of with HO.