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 |
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Pages (from-to) | 253-256 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 22 |
Issue number | 1 |
Early online date | 17 Dec 2019 |
DOIs | |
Publication status | Published - 3 Jan 2020 |
Bibliographical note
Funding Information:This work was supported by the Presidential Leadership Programme of Egypt, the European Research Council (AdG ROCOCO), and the EPSRC.
Publisher Copyright:
© 2019 American Chemical Society.