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An Aliphatic Bischler–Napieralski Reaction: Dihydropyridones by Cyclocarbonylation of 3-Allylimidazolidin-4-ones
- Source :
- Organic Letters; January 2020, Vol. 22 Issue: 1 p253-256, 4p
- Publication Year :
- 2020
-
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.
Details
- Language :
- English
- ISSN :
- 15237060 and 15237052
- Volume :
- 22
- Issue :
- 1
- Database :
- Supplemental Index
- Journal :
- Organic Letters
- Publication Type :
- Periodical
- Accession number :
- ejs51738053
- Full Text :
- https://doi.org/10.1021/acs.orglett.9b04250