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

Research output: Contribution to journal › Article (Academic Journal) › peer-review

3 Citations (Scopus)

159 Downloads (Pure)

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.

Access to Document

10.1021/acs.orglett.9b04250

Full-text PDF (author’s accepted manuscript)
This is the author accepted manuscript (AAM). The final published version (version of record) is available online via American Chemical Society at https://pubs.acs.org/doi/abs/10.1021/acs.orglett.9b04250 . Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 571 KB

Handle.net

Persistent link

Cite this

@article{7a335e29ae1a4da190035fb6c64cf4c5,

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",

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: {\textcopyright} 2019 American Chemical Society.",

year = "2020",

month = jan,

day = "3",

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

language = "English",

volume = "22",

pages = "253--256",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - An Aliphatic Bischler–Napieralski Reaction

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.

PY - 2020/1/3

Y1 - 2020/1/3

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.

UR - http://www.scopus.com/inward/record.url?scp=85077118650&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b04250

DO - 10.1021/acs.orglett.9b04250

M3 - Article (Academic Journal)

C2 - 31846338

SN - 1523-7060

VL - 22

SP - 253

EP - 256

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

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

Abstract

Bibliographical note

Access to Document

Handle.net

Other files and links

Fingerprint

Cite this