Gissot Arnaud, Volonterio Alessandro, Zanda Matteo
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.
J Org Chem. 2005 Aug 19;70(17):6925-8. doi: 10.1021/jo0509713.
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.
我们已经开发出一种简单且高产率的一步法，可直接从多种未活化的酯和原位生成的O-苄基羟胺阴离子合成异羟肟酸酯衍生物。该反应在-78℃下几分钟内即可完成。非常重要的是，该方法已成功应用于可烯醇化的酯，包括手性α-氨基酸酯和肽，未检测到α-碳上有任何外消旋化/差向异构化的痕迹。
