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A Enamide-based diastereoselective synthesis of isoindolo[2,1-a]quinolin-11(5H)-ones with three contiguous stereogenic centers

09 November 2022, Version 2
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A stereoselective synthesis of isoindolo[2,1-a]quinolin-11(5H)-ones containing three contiguous stereogenic centers is described. This Lewis-acid mediated reaction of enamides with N-aryl- affords the desired fused heterocyclic isoindolinones in high yields and diastereoselectivities. Scope and limitations of this method are discussed. The stereochemical outcome of this transformation indicates a stepwise reaction pathway.

Keywords

enamide
acyliminium ion
Povarov reaction
nitrogen heterocycle
diastereoselectivity

Supplementary materials

Title
Description
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Title
Supporting Information
Description
Experimental procedures, analytical data and copies of NMR spectra
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X-Ray data
Description
cif and checkcif files for compounds syn-11a, anti-11a, anti-11b, syn-11d, syn-11g, syn-11i and 12b (CCDC 2189964-2189970)
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Now Published

A Enamide‐Based Diastereoselective Synthesis of Isoindolo[2,1‐ a ]quinolin‐11(5 H )‐ones with Three Contiguous Stereogenic Centers [opens in a new tab]
Miro Halaczkiewicz, Harald Kelm, Georg Manolikakes journal article
European Journal of Organic Chemistry , Volume 26, Issue 5
Online publication date: Jan 09, 2023

Version History

Nov 09, 2022 Version 2

Version Notes

Syntax error under the subheading Results and Discussion - "Fehler! Verweisquelle konnte nicht gefunden werden" was corrected.

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-vh97c-v2
D O I: 10.26434/chemrxiv-2022-vh97c-v2 [opens in a new tab]

Funding

Deutsche Forschungsgemeinschaft
MA 6093/10-1
Forschungsinitiative Rheinland-Pfalz
Research Unit NanoKat

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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