Jump to main content
Jump to site search

Issue 8, 2008
Previous Article Next Article

Synthesis of carboxylic amides by ring-opening of oxazolidinones with Grignard reagents

Author affiliations

Abstract

Treatment of N-alkyl-oxazolidin-2-ones with Grignard reagents gives tertiary carboxylic amide products. Various substituted oxazolidinones can be used as illustrated with phenyl, benzyl or isopropyl groups on the 4-position, and methyl, benzyl or p-methoxybenzyl groups on the 3-position (the nitrogen atom). A selection of Grignard reagents were successful, including allyl, benzyl, alkyl and phenyl magnesium halides. The organomagnesium species attacks the carbonyl group and promotes ring-opening of the oxazolidinone. The product tertiary amides are useful substrates for stereoselective transformations and were applied to a highly selective enolate alkylation and to a ring-closing metathesis reaction to a six-membered lactam and hence a formal synthesis of the alkaloids (−)-coniine and (+)-stenusine.

Graphical abstract: Synthesis of carboxylic amides by ring-opening of oxazolidinones with Grignard reagents

Back to tab navigation

Publication details

The article was received on 17 Jan 2008, accepted on 08 Feb 2008 and first published on 27 Feb 2008


Article type: Paper
DOI: 10.1039/B800849C
Citation: Org. Biomol. Chem., 2008,6, 1410-1415
  •   Request permissions

    Synthesis of carboxylic amides by ring-opening of oxazolidinones with Grignard reagents

    D. Bensa, I. Coldham, P. Feinäugle, R. B. Pathak and R. J. Butlin, Org. Biomol. Chem., 2008, 6, 1410
    DOI: 10.1039/B800849C

Search articles by author

Spotlight

Advertisements