Organic & Biomolecular Chemistry 2006-05-07

Copper(I) mediated cross-coupling of amino acid derived organozinc reagents with acid chlorides.

Thomas Hjelmgaard, David Tanner

Index: Org. Biomol. Chem. 4(9) , 1796-805, (2006)

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Abstract

This paper describes the development of a straightforward experimental protocol for copper-mediated cross-coupling of amino acid derived beta-amido-alkylzinc iodides 1 and 3 with a range of acid chlorides. The present method uses CuCN.2LiCl as the copper source and for organozinc reagent 1 the methodology appears to be limited to reaction with more stable acid chlorides, providing the desired products in moderate yields. When applied to organozinc reagent 3, however, the protocol is more general and provides the products in good yields in all but one of the cases tested.