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

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. Copyright © 2000 John Wiley & Sons, Ltd.