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

2016; American Chemical Society; Volume: 138; Issue: 25 Linguagem: Inglês

10.1021/jacs.6b04364

1943-2984

Chang Guo, Mirco Fleige, Daniel Janßen-Müller, Constantin G. Daniliuc, Frank Glorius,

Synthetic Organic Chemistry Methods

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.