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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.