ENANTIOSELECTIVE SYNTHESIS OF 4-SUBSTITUTED PHENYLALANINES BY CROSS-COUPLING REACTIONS

Abstract The enantiomerically enriched BOC-protected (4-pinacolylborono)phenylalanine methyl ester ( 8 ) is produced via enzymatic resolution of the racemic material, or direct synthesis from the corresponding iodide (or triflate), and undergoes Suzuki-Miyaura coupling reactions with aromatic halides and triflates in the presence of catalytic amounts of PdCl 2 (dppf) to produce enantiomerically enriched 4-substituted phenylalanine derivatives.