Studies on the [2,3]-Stevens rearrangement of aziridinium

Rowlands, Gareth J and Barnes, William Kentish (2004) Studies on the [2,3]-Stevens rearrangement of aziridinium. Tetrahedron Letters, 45 (28). pp. 5347-5350. ISSN 0040-4039

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Abstract

The aziridinium ylide generated by the intramolecular reaction of a metal carbenoid tethered to a vinylaziridine undergoes [2,3]-Stevens rearrangement to furnish the indolizidine skeleton. It is essential that the correct nitrogen invertomer is used or a competing [1,5]-hydrogen shift predominates. During the preparation of a second system a 'one-pot' acylation-[3,3]-Claisen rearrangement was observed, delivering a seven-membered lactam. (C) 2004 Published by Elsevier Ltd.

Item Type: Article
Additional Information: Times Cited: 2; Keywords: vinylaziridine; aziridinium; ylide; carbene; [2,3]-Stevens rearrangement GENERATED METAL CARBENOIDS; AMMONIUM YLIDES; AZA-<2,3>-WITTIG REARRANGEMENTS; STEREOSELECTIVE-SYNTHESIS; INTRAMOLECULAR REACTION; VINYLAZIRIDINES; ALKALOIDS; PYRROLIDINES; ROUTE; (-)-EPILUPININE ISI:000222377000003
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: EPrints Services
Date Deposited: 06 Feb 2012 21:12
Last Modified: 29 Mar 2012 09:30
URI: http://sro.sussex.ac.uk/id/eprint/30151
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