Rapid Route to 3,4-Substituted Indoles via a Directed Ortho Metalation−Retro-Mannich Sequence

Rapid Route to 3,4-Substituted Indoles via a Directed Ortho Metalation−Retro-Mannich Sequence

In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)−cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37−88% yields. A conceptually new methodology to diverse 3,4-substituted indoles...

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Veröffentlicht in:Organic letters 2002-03, Vol.4 (5), p.815-817
Hauptverfasser: Chauder, Brian, Larkin, Andrew, Snieckus, Victor
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Halogens - chemistry
Indoles - chemical synthesis
Indoles - chemistry
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Zusammenfassung:In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)−cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37−88% yields. A conceptually new methodology to diverse 3,4-substituted indoles (10, 11, 13) is thereby introduced.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol017310m