Three approaches to the synthesis of β-(2)-homophenylalanine derivatives using Negishi cross-coupling reaction are reported. In the first two approaches, two protected alpha-iodoniethyl-beta-amino esters are each converted into the corresponding organozinc iodides, which then undergo Pd-catalysed cross-coupling with aromatic halides to give β(2)-homophenylalanine derivatives, and the X-ray crystal Structure of one product is reported. Alternatively, Negishi cross-coupling of the zinc reagent derived from N-benzyl 3-iodomethyl azetidin-2-one and aryl halides gave 3-benzylazetidin-2-ones, masked beta(2)-homophenylalanine derivatives. The X-ray crystal structure of 1-benzyl-3-[(p-tolunesulfonyloxy)methyl]-azetidin-2-one confirms the Structural assignment.
Bartrum, H. E., Adams, H., Caggiano, L., & Jackson, R. F. W. (2008). Synthesis of β2-homophenylalanine derivatives by Negishi cross-coupling reactions. Tetrahedron, 64(17), 3701-3712. https://doi.org/10.1016/j.tet.2008.02.024