One-step synthesis of O-benzyl hydroxamates from unactivated aliphatic and aromatic esters.
We have developed a simple and high yielding one-step method for the synthesis of hydroxamate derivatives directly from a broad range of unactivated esters and the anion of O-benzyl-hydroxylamine generated in situ. The reaction takes place in minutes at -78 degrees C. Very importantly, the method was successfully employed with enolizable esters, including chiral alpha-amino acid esters and peptides, with no trace of racemization/epimerization at the alpha carbon detected.
Gissot
Arnaud
A
C.N.R.-I.C.R.M., sezione A. Quilico and Dipartimento C.M.I.C. G. Natta, Politecnico di Milano, via Mancinelli 7, I-20131 Milan, Italy.
Volonterio
Alessandro
A
Zanda
Matteo
M
D004952:Esters / Q000737:chemistry*; D006877:Hydroxamic Acids / Q000138:chemical synthesis*
D004952:Esters; D006877:Hydroxamic Acids