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Access to functionalized Mannich scaffolds via a calcium-catalyzed dehydrative aza-Friedel-Crafts reaction

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Access to functionalized Mannich scaffolds via a calcium-catalyzed dehydrative aza-Friedel-Crafts reaction. / Basson, Ashley; McLaughlin, Mark.
In: Cell Reports Physical Science, Vol. 4, No. 4, 101234, 19.04.2023.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Basson, A & McLaughlin, M 2023, 'Access to functionalized Mannich scaffolds via a calcium-catalyzed dehydrative aza-Friedel-Crafts reaction', Cell Reports Physical Science, vol. 4, no. 4, 101234. https://doi.org/10.1016/j.xcrp.2022.101234

APA

Basson, A., & McLaughlin, M. (2023). Access to functionalized Mannich scaffolds via a calcium-catalyzed dehydrative aza-Friedel-Crafts reaction. Cell Reports Physical Science, 4(4), Article 101234. https://doi.org/10.1016/j.xcrp.2022.101234

Vancouver

Basson A, McLaughlin M. Access to functionalized Mannich scaffolds via a calcium-catalyzed dehydrative aza-Friedel-Crafts reaction. Cell Reports Physical Science. 2023 Apr 19;4(4):101234. Epub 2023 Jan 12. doi: 10.1016/j.xcrp.2022.101234

Author

Basson, Ashley ; McLaughlin, Mark. / Access to functionalized Mannich scaffolds via a calcium-catalyzed dehydrative aza-Friedel-Crafts reaction. In: Cell Reports Physical Science. 2023 ; Vol. 4, No. 4.

Bibtex

@article{aad55e49f19a43b6a4d2d5e1e55ce19b,
title = "Access to functionalized Mannich scaffolds via a calcium-catalyzed dehydrative aza-Friedel-Crafts reaction",
abstract = "The α-functionalization of amines and related scaffolds plays a key role in both target synthesis and medicinal chemistry. As such, elegant solutions employing transition metal catalysis, photoredox catalysis, and electrosynthetic methods have been described. The methods often rely on harsh activation conditions or difficult-to-access catalysts and experimental setups. Here, we report a calcium-catalyzed addition of aniline derivatives into N-acyliminium ions under mild conditions to access a diverse range of Mannich-type products. The reaction is unified and can be applied to N,O-acetal derivatives to access di-substituted amides and also isoindolinones as a method to functionalize medicinally relevant scaffolds. The reaction displays a high level of functional group tolerance and provides access to a diverse range of scaffolds.",
keywords = "calcium catalysis, N-acyliminium ions, aza-Friedel-Crafts, dehydration",
author = "Ashley Basson and Mark McLaughlin",
year = "2023",
month = apr,
day = "19",
doi = "10.1016/j.xcrp.2022.101234",
language = "English",
volume = "4",
journal = "Cell Reports Physical Science",
issn = "2666-3864",
publisher = "Cell Press",
number = "4",

}

RIS

TY - JOUR

T1 - Access to functionalized Mannich scaffolds via a calcium-catalyzed dehydrative aza-Friedel-Crafts reaction

AU - Basson, Ashley

AU - McLaughlin, Mark

PY - 2023/4/19

Y1 - 2023/4/19

N2 - The α-functionalization of amines and related scaffolds plays a key role in both target synthesis and medicinal chemistry. As such, elegant solutions employing transition metal catalysis, photoredox catalysis, and electrosynthetic methods have been described. The methods often rely on harsh activation conditions or difficult-to-access catalysts and experimental setups. Here, we report a calcium-catalyzed addition of aniline derivatives into N-acyliminium ions under mild conditions to access a diverse range of Mannich-type products. The reaction is unified and can be applied to N,O-acetal derivatives to access di-substituted amides and also isoindolinones as a method to functionalize medicinally relevant scaffolds. The reaction displays a high level of functional group tolerance and provides access to a diverse range of scaffolds.

AB - The α-functionalization of amines and related scaffolds plays a key role in both target synthesis and medicinal chemistry. As such, elegant solutions employing transition metal catalysis, photoredox catalysis, and electrosynthetic methods have been described. The methods often rely on harsh activation conditions or difficult-to-access catalysts and experimental setups. Here, we report a calcium-catalyzed addition of aniline derivatives into N-acyliminium ions under mild conditions to access a diverse range of Mannich-type products. The reaction is unified and can be applied to N,O-acetal derivatives to access di-substituted amides and also isoindolinones as a method to functionalize medicinally relevant scaffolds. The reaction displays a high level of functional group tolerance and provides access to a diverse range of scaffolds.

KW - calcium catalysis

KW - N-acyliminium ions

KW - aza-Friedel-Crafts

KW - dehydration

U2 - 10.1016/j.xcrp.2022.101234

DO - 10.1016/j.xcrp.2022.101234

M3 - Journal article

VL - 4

JO - Cell Reports Physical Science

JF - Cell Reports Physical Science

SN - 2666-3864

IS - 4

M1 - 101234

ER -