Iridium-Catalyzed Regio- and Enantioselective N-Allylation of Indoles

Iridium is blind to C: Highly regio‐ and enantioselective, iridium‐catalyzed N‐allylations of indoles, which complement the more common reactivity of indoles as carbon nucleophiles, have been developed (see scheme). These reactions form highly enantioenriched N‐allylindoles, which are readily transf...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (42), p.7841-7844
Hauptverfasser: Stanley, Levi M, Hartwig, John F
Format: Artikel
Sprache:eng
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Zusammenfassung:Iridium is blind to C: Highly regio‐ and enantioselective, iridium‐catalyzed N‐allylations of indoles, which complement the more common reactivity of indoles as carbon nucleophiles, have been developed (see scheme). These reactions form highly enantioenriched N‐allylindoles, which are readily transformed into enantioenriched 3‐(1H‐indol‐1‐yl)‐N‐methyl‐3‐aryl propan‐1‐amines, dihydropyrrolo[1,2‐a]indoles, and indol‐1‐yl propanoic acids.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200904338