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Studies on the [2,3]-Stevens rearrangement of aziridinium
journal contribution
posted on 2023-06-08, 09:14 authored by Gareth J Rowlands, William Kentish BarnesThe 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.
History
Publication status
- Published
Journal
Tetrahedron LettersISSN
0040-4039Publisher
ElsevierExternal DOI
Issue
28Volume
45Page range
5347-5350Department affiliated with
- Chemistry Publications
Notes
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:000222377000003Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2012-02-06Usage metrics
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