Abstract
The N-chloroformylimidazolidinone derivative of enantiopure l-alanine was deprotonated to form an enolate and functionalized with a series of allylic halides. Treatment of the resulting carbamoyl chlorides with potassium iodide led to cyclization of the allylic substituent onto the carbonyl group in an intramolecular aliphatic Friedel–Crafts-type acylation that corresponds to an aliphatic Bischler–Napieralski reaction. The product 3,4-dihydropyridinones were amenable to further functionalization, and finally hydrolysis, to deliver a series of enantio-enriched pipecolic acid derivatives.
| Original language | English |
|---|---|
| Pages (from-to) | 253-256 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Early online date | 17 Dec 2019 |
| DOIs | |
| Publication status | Published - 3 Jan 2020 |
Bibliographical note
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Cite this
Amer, M. M., Olaizola, O., Carter, J., Abas, H., & Clayden, J. (2020). An Aliphatic Bischler–Napieralski Reaction: Dihydropyridones by Cyclocarbonylation of 3-Allylimidazolidin-4-ones. Organic Letters, 253-256. https://doi.org/10.1021/acs.orglett.9b04250