Transesterifications mediated by t-BuNH2
Suárez Castillo, Oscar Rodolfo
2008
Suárez-Castillo Oscar R., Montiel-Ortega Luis Alberto, Fragoso-Vázquez Manuel Jonathan, Meléndez-Rodríguez Myriam, Sánchez-Zavala Maricruz, Transesterifications mediated by t-BuNH2. Tetrahedron Lett. 49, 996999 (2008). ISSN 0040-4039. doi:10.1016/j.tetlet.2007.12.013
Abstract
A mild protocol for transesterification of simple esters is described. The method is based on the use of t-BuNH2/ROH (R = Me, Et, i-Pr, t-Bu) with or without LiBr. The scope of the procedure was explored for aliphatic and aromatic esters. The protocol is particularly useful when going from higher to lower hindered esters and harsh reaction conditions are needed for the reversal process. A rationalization of the mechanism is presented. The scope and limitation of this transformation are also described.
Artículos relacionados
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
Synthesis of Acetamido(indol-3-yl)propanol Derivatives
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea