Cambridge Open Engage home
What is Cambridge Open Engage?
How to Submit
Browse
About
News [opens in a new tab]

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
Actions
Title
Supporting Information
Description
Experimental procedures, analytical data and copies of NMR spectra
Actions
Title
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)
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.

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.

Metrics

644
424
0
Views
Downloads
Citations

License

CC logo
CC
BY logo
BY
NC logo
NC
ND logo
ND
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

Share