Literature DB >> 12323014

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

Mukund P Sibi1, Hikaru Hasegawa, Sandeep R Ghorpade.   

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]

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Year:  2002        PMID: 12323014     DOI: 10.1021/ol0263301

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Preparation of bifunctional isocyanate hydroxamate linkers: Synthesis of carbamate and urea tethered polyhydroxamic acid chelators.

Authors:  Rasika Fernando; Jonathan M Shirley; Emilio Torres; Hollie K Jacobs; Aravamudan S Gopalan
Journal:  Tetrahedron Lett       Date:  2012-11-21       Impact factor: 2.415

2.  Reactions of N-benzyloxycarbamate derivatives with stabilized carbon nucleophiles: a new synthetic approach to polyhydroxamic acids and other hydroxamate-containing mixed ligand systems.

Authors:  Yuan Liu; Hollie K Jacobs; Aravamudan S Gopalan
Journal:  J Org Chem       Date:  2009-01-16       Impact factor: 4.354

3.  Amide Activation in Ground and Excited States.

Authors:  Ervin Kovács; Balázs Rózsa; Attila Csomos; Imre G Csizmadia; Zoltán Mucsi
Journal:  Molecules       Date:  2018-11-02       Impact factor: 4.411

  3 in total

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