Palladium(O) catalysed and copper(I) promoted reactions of the secondary zinc reagent derived from L-threonine

Article abstract of DOI:10.1039/b208667k

The preparation of C-3 epimeric secondary zinc reagents from diastereoisomeric iodide using DMF as solvent was discussed and analyzed by NMR methods. Palladium catalysed cross couplings and copper promoted allylations produced protected β-methyl substituted amino acids. It was concluded that the threonine derived zinc reagents were of limited values, but further optimization of copper-promoted reactions make this approach to synthesis of β-methyl substituted α-amino acids more useful.