Catechol and Substituted Catechol-Derived Ortho Esters, Models for Protected Active Esters in Peptide Synthesis

Article abstract of DOI:10.1021/jo00328a020

Monoalkyl orthoacetates derived from catechol, 4-nitrocatechol, and tetrabromocatechol have been prepared, and mild conditions (NaI-BF3OEt2) have been found that convert them to the corresponding catechol monoacetates in high yield.Possible applications of ortho esters as protected active esters for peptide synthesis are discussed.