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



: Chen XY, Liu Q, Chauhan P, Li S, Peuronen A, Rissanen K, Jafari E, Enders D

Publisher: WILEY-V C H VERLAG GMBH

: 2017

: Angewandte Chemie International Edition

: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

: ANGEW CHEM INT EDIT

: 56

: 22

: 6241

: 6245

: 5

: 1433-7851

DOI: https://doi.org/10.1002/anie.201702881


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.



Last updated on 2024-26-11 at 23:52