Synthesis of [2,3,3,2'3',5',6' -2H7]-L-tyrosine from phenol-d6

Article abstract of DOI:10.1002/1099-1344(200008)43:9<917::AID-JLCR377>3.0.CO;2-5

An enantioselective synthesis of [2,3,3,2'3',5',6'-²H₇]-L-tyrosine is described. Z-3-(4-acetoxy-2,3,5,6-²H₄-phenyl)-3-²H-2-acetylamino acrylic acid was prepared in five steps from phenol-d₆. Chiral reduction of the olefin followed by removal of the acetate protecting groups furnished the d₇-amino acid in high ee.