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Angew Chem Int Ed Engl. 2013 Sep 27;52(40):10630-4. doi: 10.1002/anie.201304919. Epub 2013 Aug 16.

Rhodium-catalyzed dynamic kinetic asymmetric transformations of racemic allenes by the [3+2] annulation of aryl ketimines.

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  • 1Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015 Lausanne (Switzerland) http://isic.epfl.ch/lcsa.

Abstract

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.

Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS:

CH activation; DYKAT; allenes; asymmetric catalysis; rhodium

PMID:
23956126
[PubMed - indexed for MEDLINE]
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