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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 Barnes
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.

History

Publication status

  • Published

Journal

Tetrahedron Letters

ISSN

0040-4039

Publisher

Elsevier

Issue

28

Volume

45

Page range

5347-5350

Department 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:000222377000003

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-02-06

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