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N-Heterocyclic Carbene Catalyzed [4+2] Annulation of Enals via a Double Vinylogous Michael Addition: Asymmetric Synthesis of 3,5-Diaryl Cyclohexenones
Tekijät: Chen XY, Liu Q, Chauhan P, Li S, Peuronen A, Rissanen K, Jafari E, Enders D
Kustantaja: WILEY-V C H VERLAG GMBH
Julkaisuvuosi: 2017
Journal: Angewandte Chemie International Edition
Tietokannassa oleva lehden nimi: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Lehden akronyymi: ANGEW CHEM INT EDIT
Vuosikerta: 56
Numero: 22
Aloitussivu: 6241
Lopetussivu: 6245
Sivujen määrä: 5
ISSN: 1433-7851
DOI: https://doi.org/10.1002/anie.201702881
Tiivistelmä
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.
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.
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