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Brønsted-Acid Catalyzed Diastereoselective Synthesis of Spiroisoindolinones from Enamides

04 March 2024, Version 3
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A highly diastereoselective synthesis of spiroisoindolinones from enamides and 3-hydroxy-isoindolinones is reported. The reaction proceeds rapidly in the presence of para-toluenesulfonic acid as Brønsted acid-catalyst and affords a variety of densely substituted spiroisoindolinoes with three contiguous stereogenic centers in high yields (up to 98%) and diastereoselectivities (up to dr >98:<2:0:0).

Keywords

spirocycles
enamide
stereoselective synthesis
spiroisindolinones

Supplementary materials

Title
Description
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Title
Supporting Information File 1
Description
Experimental details, spectral data, DOIs for data referring to this study (deposited in the chemotion repository: https://www.chemotion-repository.net/), and copies of NMR spectra for all new compounds
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Supporting Information File 2
Description
Information on the physical availability of the target com-pounds from the Molecule Archive at KIT (https://compound-platform.eu/home).
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X ray data
Description
cif and checkcif files for compounds 4a (CCDC 2311285), 4h (CCDC 2311286) and 4p (CCDC 2311287)
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Comment number 1, Chenxiao QIAN: Mar 05, 2024, 06:01

The reactions mentioned in Scheme 1b have been reported earlier. Org. Chem. Front. 2022, 9, 1234– 1240, DOI: 10.1039/D1QO01864G.

Now Published

Brønsted Acid-Catalyzed Diastereoselective Synthesis of Spiroisoindolinones from Enamides [opens in a new tab]
Miro Halaczkiewicz, Arianit Maraj, Harald Kelm, Georg Manolikakes journal article
Organic Letters , Volume 26, Issue 11
Online publication date: Mar 11, 2024

Version History

Mar 04, 2024 Version 3

Version Notes

A new version of Supporting Information file 1 is provided. Due to an error in transferring data from the original cif files to the SI some cell parameters (cell parameter β for compound 4p and cell parameters α, β and γ for compound 4h) were transferred incorrectly. The revised SI contains the corrected/valid cell parameters for compounds 4p and 4 h, as deposited in the CDC.

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

DOI

10.26434/chemrxiv-2023-n809t-v3
D O I: 10.26434/chemrxiv-2023-n809t-v3 [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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