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This work was supported in part by a research grant from the U.S. National Institutes of Health (R01A112503-01A2). H.A.S. is the recipient of the Kilpatrick fellowship 2007–2008.
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Stable Aziridinium Salts as Versatile Intermediates: Isolation and Regio- and Stereoselective Ring-Opening and Rearrangement†
Article first published online: 13 JAN 2009
DOI: 10.1002/anie.200805244
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Song, Hyun A., Dadwal, M., Lee, Y., Mick, E. and Chong, H.-S. (2009), Stable Aziridinium Salts as Versatile Intermediates: Isolation and Regio- and Stereoselective Ring-Opening and Rearrangement. Angew. Chem. Int. Ed., 48: 1328–1330. doi: 10.1002/anie.200805244
- †
Publication History
- Issue published online: 28 JAN 2009
- Article first published online: 13 JAN 2009
- Manuscript Received: 27 OCT 2008
Funded by
- National Institutes of Health. Grant Number: R01A112503-01A2
Corrected by:
Vol. 49, Issue 49, 9311, Article first published online: 1 DEC 2010
Keywords:
- aziridinium ions;
- rearrangement;
- regioselectivity;
- strained molecules
Abstract
Rock trapping and exploration: Aziridinium bromide salts were discovered serendipitously during bromination of N,N-dicarboxymethylated β-amino alcohols. Regiospecific ring-opening and rearrangement of the isolated, surprisingly stable aziridinium salts produces useful molecules including C-functionalized oxomorpholines and α,β-unsaturated amines.