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One-Step Synthesis of O-Benzyl Hydroxamates from Unactivated Aliphatic and Aromatic Esters

Supporting Info

Arnaud Gissot,* Alessandro Volonterio, and Matteo Zanda*

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 matteo.zanda@polimi.it

J. Org. Chem., 2005, 70 (17), pp 6925–6928

DOI: 10.1021/jo0509713

Publication Date (Web): July 13, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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 °C. Very importantly, the method was successfully employed with enolizable esters, including chiral α-amino acid esters and peptides, with no trace of racemization/epimerization at the α carbon detected.

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