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Asymmetric alkylation of N-acylisoindolin-1-ones via α-bromoimides: A novel route to 1-substituted isoindolines

✍ Scribed by Andreas Müller; Kurt Polborn; Klaus T. Wanner

Publisher: Journal of Heterocyclic Chemistry
Year: 2007
Tongue: English
Weight: 1009 KB
Volume: 44
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570440312

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✦ Synopsis

Abstract

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Key intermediate in the synthesis of the title compounds 9a‐c and 10a‐c was the chiral α‐bromoimide 1 which has been prepared by radical bromination of the corresponding N‐acylisoindolin‐1‐one 13. 1 was alkylated with silyl enol ethers under Lewis acid catalysis using α‐amidoalkylation methodology. N,N‐diacyliminium ion 14 is presumably the intermediate in this reaction. Further transformations of the alkylated compounds yielded 1‐substituted isoindolines as target compounds.

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