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Full Paper
Ring Expansion Induced by DAST: Synthesis of Substituted 3-Fluoropiperidines from Prolinols and 3-Fluoroazepanes from 2-Hydroxymethylpiperidines
Article first published online: 30 JUL 2007
DOI: 10.1002/ejoc.200700237
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Déchamps, I., Gomez Pardo, D. and Cossy, J. (2007), Ring Expansion Induced by DAST: Synthesis of Substituted 3-Fluoropiperidines from Prolinols and 3-Fluoroazepanes from 2-Hydroxymethylpiperidines. Eur. J. Org. Chem., 2007: 4224–4234. doi: 10.1002/ejoc.200700237
Publication History
- Issue published online: 10 AUG 2007
- Article first published online: 30 JUL 2007
- Manuscript Received: 15 MAR 2007
Funded by
- Johnson & Johnson
- Abstract
- Article
- References
- Cited By
Keywords:
- Ring expansion;
- Rearrangement;
- Fluorine;
- Aziridinium;
- Nitrogen heterocycles
Abstract
Optically active prolinols can be converted into optically active 3-fluoropiperidines by treatment with DAST. The reaction often produces 2-fluoromethylpyrrolidines as byproducts. The ring expansion was also applied to 2-hydroxypiperidines to produce 3-fluoroazepanes. The rearrangement proceeds via an aziridinium intermediate. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)