Synthesis of β2-homophenylalanine derivatives by Negishi cross-coupling reactions

Reference:

Bartrum, H. E., Adams, H., Caggiano, L. and Jackson, R. F. W., 2008. Synthesis of β2-homophenylalanine derivatives by Negishi cross-coupling reactions. Tetrahedron, 64 (17), pp. 3701-3712.

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Official URL:

http://dx.doi.org/10.1016/j.tet.2008.02.024

Abstract

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.

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