Stereocontrolled synthesis of hydroxymethylene phosphonate analogues of phosphorylated tyrosine and their conversion to monofluoromethylene phosphonate analogues

Article abstract of DOI:10.1016/0040-4020(96)00671-0

A stereocontrolled synthesis of protected variants 13 and 15 of HPmp 2, a mimic of phosphorylated tyrosine, was achieved through either chiral-auxiliary assisted or chiral heterobimetal catalyzed stereoselective hydrophosphonylation of 4-formyl-L-phenylalanine derivative 7. Fluorination of HPmp derivatives 13 and 15 thus obtained was carried out to give FPmp derivatives 16 and 17.