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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
Author(s) -
Chen XiangYu,
Liu Qiang,
Chauhan Pankaj,
Li Sun,
Peuronen Anssi,
Rissanen Kari,
Jafari Ehsan,
Enders Dieter
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201702881
Subject(s) - annulation , michael reaction , carbene , catalysis , chemistry , organocatalysis , organic chemistry , enantioselective synthesis
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.