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

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

doi:10.1021/acs.orglett.9b04250

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

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

School of Chemistry

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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 language	English
Pages (from-to)	253-256
Number of pages	4
Journal	Organic Letters
Volume	22
Issue number	1
Early online date	17 Dec 2019
DOIs	https://doi.org/10.1021/acs.orglett.9b04250
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.

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

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.",

author = "Amer, {Mostafa M.} and Olatz Olaizola and Jennifer Carter and Hossay Abas and Jonathan Clayden",

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doi = "10.1021/acs.orglett.9b04250",

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T2 - Dihydropyridones by Cyclocarbonylation of 3-Allylimidazolidin-4-ones

AU - Amer, Mostafa M.

AU - Olaizola, Olatz

AU - Carter, Jennifer

AU - Abas, Hossay

AU - Clayden, Jonathan

N1 - 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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N2 - 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.

AB - 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.

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

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