Asymmetric Pd-Catalyzed Alkene Carboamination Reactions for the Synthesis of 2‑Aminoindane Derivatives

A new type of Pd-catalyzed alkene carboamination reaction that provides direct access to enantioenriched 2-aminoindanes from 2-allylphenyltriflate derivatives and aliphatic amines is described. A catalyst generated in situ from Pd­(OAc)2 and (S)-tert-butylPHOX provides the functionalized carbocycles...

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Veröffentlicht in:Journal of the American Chemical Society 2015-09, Vol.137 (35), p.11246-11249
Hauptverfasser: White, Derick R, Hutt, Johnathon T, Wolfe, John P
Format: Artikel
Sprache:eng
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Zusammenfassung:A new type of Pd-catalyzed alkene carboamination reaction that provides direct access to enantioenriched 2-aminoindanes from 2-allylphenyltriflate derivatives and aliphatic amines is described. A catalyst generated in situ from Pd­(OAc)2 and (S)-tert-butylPHOX provides the functionalized carbocycles in good yield with up to >99:1 er. The transformations occur via a key anti-aminopalladation that involves intermolecular attack of an amine nucleophile on an arylpalladium alkene complex.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b07203