Rhodium-Catalyzed Dynamic Kinetic Asymmetric Transformations of Racemic Allenes by the [3+2] Annulation of Aryl Ketimines

Racemization required: Rhodium(I)‐catalyzed CH activation directed by unprotected ketimines initiates selective [3+2] cycloaddition with allenes, providing access to highly substituted indenylamines. The reaction proceeds through the dynamic kinetic asymmetric transformation of racemic allenes. The...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-09, Vol.52 (40), p.10630-10634
Hauptverfasser: Tran, Duc N., Cramer, Nicolai
Format: Artikel
Sprache:eng
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Zusammenfassung:Racemization required: Rhodium(I)‐catalyzed CH activation directed by unprotected ketimines initiates selective [3+2] cycloaddition with allenes, providing access to highly substituted indenylamines. The reaction proceeds through the dynamic kinetic asymmetric transformation of racemic allenes. The catalyst controls the enantio‐ and diastereoselectivity, the regioselectivities of the CH activation and allene incorporation, as well as the E/Z ratio.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201304919