Issue 8, 2008

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

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

Article information

Article type
Paper
Submitted
17 Jan 2008
Accepted
08 Feb 2008
First published
27 Feb 2008

Org. Biomol. Chem., 2008,6, 1410-1415

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements