Catalytic Oxyamidation of Indoles

Catalytic Oxyamidation of Indoles

Twofold versatility: An efficient intermolecular oxyamidation of indoles relies on the application of rhodium(II)‐catalyzed nitrene transfers. The cis or trans products are exclusively isolated in very good yields (up to 88 %) by changing the nucleophile. Control of the regioselectivity of the addit...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2010-02, Vol.49 (9), p.1634-1637
Hauptverfasser: Beaumont, Stéphane, Pons, Valérie, Retailleau, Pascal, Dodd, Robert H, Dauban, Philippe
Format: Artikel
Sprache:eng
Schlagworte:
aminohydroxylation
aziridines
Catalysis
Chemical Sciences
Imines - chemistry
Indole Alkaloids - chemistry
indoles
Indoles - chemistry
Isomerism
nitrenes
Organic chemistry
Oxidation-Reduction
rhodium
Rhodium - chemistry
Stereoisomerism
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Beschreibung
Zusammenfassung:Twofold versatility: An efficient intermolecular oxyamidation of indoles relies on the application of rhodium(II)‐catalyzed nitrene transfers. The cis or trans products are exclusively isolated in very good yields (up to 88 %) by changing the nucleophile. Control of the regioselectivity of the addition is also possible by modifying the substitution of the indole double bond (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200906650