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

Peng Bo | Zendy; O'Donovan Daniel H. | Zendy; Jurberg Igor D. | Zendy; Maulide Nuno | Zendy

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

Author(s) -

Peng Bo,

O'Donovan Daniel H.,

Jurberg Igor D.,

Maulide Nuno

Publication year - 2012

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201203293

Subject(s) - electrophile , iminium , in situ , amide , nucleophile , dual (grammatical number) , chemistry , combinatorial chemistry , dual role , polymer chemistry , organic chemistry , catalysis , art , literature

Rearranging its feathers : 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.

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