A convenient method for the conversion of N-acyloxazolidinones to hydroxamic acids

Mukund P Sibi; Hikaru Hasegawa; Sandeep R Ghorpade

doi:10.1021/ol0263301

A convenient method for the conversion of N-acyloxazolidinones to hydroxamic acids

Org Lett. 2002 Oct 3;4(20):3343-6. doi: 10.1021/ol0263301.

Authors

Mukund P Sibi¹, Hikaru Hasegawa, Sandeep R Ghorpade

Affiliation

¹ Department of Chemistry, North Dakota State University, Fargo, ND 58015, USA. [email protected]

PMID: 12323014
DOI: 10.1021/ol0263301

Abstract

Treatment of N-acyloxazolidinones with hydroxylamines using samarium triflate as a Lewis acid provides the corresponding hydroxamic acids in 50-98% yields at room temperature. The conversion proceeds with high degree of chemoselectivity and without racemization of chiral centers alpha- to the acyl group. [reaction: see text]

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Hydroxamic Acids / chemical synthesis*
Hydroxamic Acids / chemistry
Isomerism
Mesylates / chemistry
Molecular Structure
Oxazolidinones / chemistry*
Temperature

Substances

Hydroxamic Acids
Mesylates
Oxazolidinones
trifluoromethanesulfonic acid

Grants and funding

1P20 RR 15566-01/RR/NCRR NIH HHS/United States