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 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.
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstraße 40, 48149 Münster, Germany.
Chang
C
Guo
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstraße 40, 48149 Münster, Germany.
Mirco
M
Fleige
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstraße 40, 48149 Münster, Germany.
Daniel
D
Janssen-Müller
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstraße 40, 48149 Münster, Germany.
Constantin G
CG
Daniliuc
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstraße 40, 48149 Münster, Germany.
Frank
F
Glorius