Nitroacetyl Group as a Peptide Synthon: Synthesis of Dipeptides with an α,α-Bisallylglycine Residue at the N-Terminus

Article abstract of DOI:10.1002/hlca.19910740516

N-Nitroacetyl derivatives of L-proline, L-valine, and L-phenylalanine esters were prepared in two steps under mild conditions (Scheme 2).Regiospecific mono- and bis-allylation of these nitroacetyl derivatives were accomplished in presence of a Pd(0) catalyst.The bis-allyl derivatives 7-9 were obtained in 40-75 percent yield.The tertiary NO2 group in these compounds could be transformed into an acetylamino group by Zn/AcOH/Ac2O.The final products 11-13 are dipeptides in which the N-terminal glycine residue bears two α-allyl substituents.