Dual nucleophilic/electrophilic capture of in situ generated iminium ethers: towards the synthesis of functionalized amide building blocks.

Authors :: Peng B
O'Donovan DH
Jurberg ID
Maulide N
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2012 Dec 14; Vol. 18 (51), pp. 16292-6. Date of Electronic Publication: 2012 Nov 14.
Publication Year :: 2012
Abstract: 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.<br /> (Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

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