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Electrophilic Amide Activation

The selective activation of amides with suitable electrophilic reagents allows access to novel reactivity manifolds and opens up intriguing perspectives in synthesis. We have previously reported on the discovery of new pericyclic domino transformations of keteniminium salts generated via electrophilic activation of amides. 

(For an own review, see: Chem. Asian J. 2011, 6, 2224-2239)


Recent highlights of this chemistry include:

(a) the development of one-pot sequences allowing the ability to achieve multiple (up to three), different C-C bond forming events in a single operation


m. Eur. J. 2012, 18, 16292-16296

(b) the establishment of a novel methodology for direct lactonisation of ethers and alcohols onto amides

 Chem. Eur. J. 2013, 19, 2606-2610

(c) a new traceless asymmetric α-allylation that relies on the use of pseudoephedrine amides and complements the well-known Myers asymmetric alkylation reaction


 J. Am. Chem. Soc. 2013, 135, 14968-14971


Organic Synthesis
Department of Organic Chemistry
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