R. Hoffman, H. Kim
Apr 10, 1992
Citations
0
Influential Citations
29
Citations
Journal
Tetrahedron
Abstract
Abstract (R)-2-Azidoesters and their derived (R)-2-azido acids are readily prepared from common amino acids by an inversion methodology that employs (S)-2-nosyloxyesters as key intermediates. The (R)-2- azidoesters can be used as protected amino acid equivalents in peptide synthesis. Basic hydrolysis frees the carboxyl group. Triphenylphosphine/water is used to free the amine group. By these reactions a variety of L- D and D-L dipeptides,L-D-L tripeptides,and depsipeptides can be prepared easily in good yields, and without detectable epimerization.