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Asymmetric alkylation of N‐acylisoindolin‐1‐ones via α‐bromoimides: A novel route to 1‐substituted isoindolines
Author(s) -
Müller Andreas,
Polborn Kurt,
Wanner Klaus T.
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440312
Subject(s) - chemistry , alkylation , enol , catalysis , silylation , lewis acids and bases , medicinal chemistry , combinatorial chemistry , halogenation , organic chemistry
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.