A Concise β-Lactam Route to Short Peptide Segments Containing β,β-Disubstituted β-Amino Acids

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Abstract
An efficient epimerization-free route toward β,β-disubstituted β-amino acid-containing peptides is described. The methodology involves the use of 4,4-disubstituted-N-Boc β-lactams as acylating agents, which upon coupling with amino acid esters, promoted by potassium cyanide, give rise to dipeptides with no appreciable racemization. By this procedure short peptide segments containing a four-, five-, or six-membered ring at the β-position of the β-amino acid residue have been prepared. The method has also proven to be valuable for the preparation of tripeptides. In addition the sterically hindered amino terminus of the β-amino acid can undergo peptide couplings under standard conditions.