Cooperative N‑Heterocyclic Carbene/Palladium-Catalyzed Enantioselective Umpolung Annulations

A combination of NHC organocatalysis and transition-metal catalysis gives rise to fundamentally new cooperative reactivity and enables the regio- and enantioselective annulation reaction between enals and vinyl benzoxazinanones. The cooperative umpolung annulation eliminates mutual deactivation and...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2016-06, Vol.138 (25), p.7840-7843
Main Authors: Guo, Chang, Fleige, Mirco, Janssen-Müller, Daniel, Daniliuc, Constantin G, Glorius, Frank
Format: Article
Language:English
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Summary:A combination of NHC organocatalysis and transition-metal catalysis gives rise to fundamentally new cooperative reactivity and enables the regio- and enantioselective annulation reaction between enals and vinyl benzoxazinanones. The cooperative umpolung annulation eliminates mutual deactivation and leads to a diverse set of benzazepine derivatives in good yields with excellent enantioselectivities (up to 99% ee). The development of such a cooperative catalytic system dramatically expands the scope of NHC organocatalysis by opening up new metal-catalyzed reaction pathways for homoenolate intermediates.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b04364