Lithiated Benzothiophenes and Benzofurans Require 2-Silyl Protection to Avoid Anion Migration

Lithiated Benzothiophenes and Benzofurans Require 2-Silyl Protection to Avoid Anion Migration

ABSTRACT 2-Trimethylsilyl protection of benzothiophenes and benzofurans prevents anion migration to the 2-position when lithiated species are formed. These lithiated benzothiophenes and benzofurans provide superior results in additions to piperidones. De­protection is conveniently achieved under aci...

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Veröffentlicht in:Synlett 2004-07, Vol.2004 (8), p.1351-1354
Hauptverfasser: Hansen, Marvin M., Clayton, Marcella T., Godfrey, Alexander G., Grutsch Jr, John L., Keast, Sandra S., Kohlman, Dan T., McSpadden, Andreea R., Pedersen, Steven W., Ward, Jeffrey A., Xu, Yao-Chang
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Sprache:eng
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Zusammenfassung:ABSTRACT 2-Trimethylsilyl protection of benzothiophenes and benzofurans prevents anion migration to the 2-position when lithiated species are formed. These lithiated benzothiophenes and benzofurans provide superior results in additions to piperidones. De­protection is conveniently achieved under acidic conditions. Direct C-7 metalation of benzothiophene is enabled by 2-triisopropylsilyl protection at C-2.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2004-825609