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

Arnaud Gissot | Zendy; Alessandro Volonterio | Zendy; Matteo Zanda | Zendy

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

Author(s) -

Arnaud Gissot,

Alessandro Volonterio,

Matteo Zanda

Publication year - 2005

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo0509713

Subject(s) - chemistry , racemization , epimer , hydroxylamine , organic chemistry , combinatorial chemistry

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.

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