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

Ashley J. Basson, Mark G. McLaughlin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)
26 Downloads (Pure)

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.
Original languageEnglish
Article number101234
JournalCell Reports Physical Science
Volume4
Issue number4
Early online date12 Jan 2023
DOIs
Publication statusPublished - 19 Apr 2023
Externally publishedYes

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