An Aliphatic Bischler–Napieralski Reaction: Dihydropyridones by Cyclocarbonylation of 3-Allylimidazolidin-4-ones

Mostafa M. Amer, Olatz Olaizola, Jennifer Carter, Hossay Abas, Jonathan Clayden

Research output: Contribution to journalArticle (Academic Journal)peer-review

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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 languageEnglish
Pages (from-to)253-256
Number of pages4
JournalOrganic Letters
Volume22
Issue number1
Early online date17 Dec 2019
DOIs
Publication statusPublished - 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.

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