Reddy, D. Srinivasa ; Judd, Weston R. ; Aubé, Jeffrey (2003) Lewis Acid-Mediated Reactions of Alkyl Azides with α,β-Unsaturated Ketones Organic Letters, 5 (21). pp. 3899-3902. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/ol0355130
Related URL: http://dx.doi.org/10.1021/ol0355130
Abstract
Alkyl azides react with saturated ketones upon treatment with Lewis acids to afford ring-expansion products through the azido-Schmidt reaction, but this reaction does not proceed when α,β-unsaturated ketones are used. In this study, alkyl azides were reacted with enones in the presence of Lewis acids to give enaminones (vinylogous amides), which formally involve a ring contraction reaction. The mechanism and scope of this reaction is discussed.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society |
| ID Code: | 122027 |
| Deposited On: | 27 Jul 2021 10:31 |
| Last Modified: | 27 Jul 2021 10:31 |
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