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Dual Nucleophilic/Electrophilic Capture of In Situ Generated Iminium Ethers: Towards the Synthesis of Functionalized Amide Building Blocks

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Peng,  Bo
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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O'Donovan,  Daniel H.
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Jurberg,  Igor Dias
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Maulide,  Nuno
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Peng, B., O'Donovan, D. H., Jurberg, I. D., & Maulide, N. (2012). Dual Nucleophilic/Electrophilic Capture of In Situ Generated Iminium Ethers: Towards the Synthesis of Functionalized Amide Building Blocks. Chemistry-a European Journal, 18(51), 16292-16296. doi:10.1002/chem.201203293.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0010-21A3-2
Abstract
The transformation of simple linear amides into a diverse range of branched, functionalized products by conversion to iminium esters is followed by sequential treatment with nucleophiles and electrophiles (see scheme). The method takes advantage of a novel Claisen rearrangement and the use of aromatic substrates greatly facilitates the formation of the intermediate iminium ether.