Iodide Dealkylation of Benzyl, PMB, PNB, and t-Butyl N-Acyl Amino Acid Esters via lithium Ion Coordination

Article abstract of DOI:10.1016/S0040-4039(00)77156-5

Lithium iodide promotes ester dealkylation in compounds containing an amide carbonyl in the γ-position to the ester carbonyl, as is found in N-acyl amino acid esters.Activation of the ester carbonyl via lithium ion coordination is facilatated by aprotic non-polar solvents such as THF and EtOAc.This process is not limited to methyl esters but readily dealkylates benzyl, PMB, PNB, and t-butyl esters and is espesially suitable for use with β-lactam esters because of the mild conditions. - Key Words: ester dealkylation; deesterification; lithium iodide; N-acyl amino acid esters; beta-lactams.