3 years ago

N-Heterocyclic Carbene Catalyzed [4+2] Annulation of Enals via a Double Vinylogous Michael Addition: Asymmetric Synthesis of 3,5-Diaryl Cyclohexenones

N-Heterocyclic Carbene Catalyzed [4+2] Annulation of Enals via a Double Vinylogous Michael Addition: Asymmetric Synthesis of 3,5-Diaryl Cyclohexenones
Kari Rissanen, Qiang Liu, Ehsan Jafari, Pankaj Chauhan, Anssi Peuronen, Sun Li, Xiang-Yu Chen, Dieter Enders
A strategy for the N-heterocyclic carbene (NHC) catalyzed asymmetric synthesis of 3,5-diaryl substituted cyclohexenones has been developed via oxidative [4+2] annulation of enals and alkenylisoxazoles. It is the first example of using NHC organocatalysis in a double vinylogous Michael type reaction, a challenging but highly desirable topic. This unprecedented protocol affords good yields as well as high to excellent diastereo- and enantioselectivities. N-heterocyclic carbene organocatalysis allows the [4+2] annulation of enals with electron-deficient 2,4-dienes via a double vinylogous Michael addition sequence. The corresponding 3,5-diaryl cyclohexenones are obtained in good to excellent yields with high to excellent diastereo- and enantioselectivities.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702881

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