Tandem aza-Claisen rearrangement and ring closing metathesis reactions: the stereoselective synthesis of functionalised carbocyclic amides

Swift, M.D., Donaldson, A. and Sutherland, A. (2009) Tandem aza-Claisen rearrangement and ring closing metathesis reactions: the stereoselective synthesis of functionalised carbocyclic amides. Tetrahedron Letters, 50(26), pp. 3241-3244. (doi: 10.1016/j.tetlet.2009.02.032)

Abstract

A one-pot, tandem process has been developed for the efficient synthesis of functionalised carbocyclic amides. A substituted cyclopentenyl trichloroacetamide was synthesised using a tandem thermal aza-Claisen rearrangement and RCM process, while an analogous cyclohexenyl trichloroacetamide was generated with high diastereoselectivity using a tandem MOM-ether directed metal-catalysed aza-Claisen rearrangement and RCM process.

• Item Type: Articles
• Keywords: Tandem reactions, ring-closing metathesis, aza-Claisen rearrangements, carbocyclic amides
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Sutherland, Professor Andrew
• Authors: Swift, M.D., Donaldson, A., and Sutherland, A.
• Subjects: Q Science > QD Chemistry
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron Letters
• Publisher: Elsevier
• ISSN: 0040-4039
• Published Online: 08 February 2009
• Copyright Holders: Copyright © 2009 Elsevier
• First Published: First published in Tetrahedron Letters 50(26):3241-3244
• Publisher Policy: Reproduced in accordance with the copyright policy of the publisher.