Asymmetric Aminative Dearomatization of 2-Naphthols via Non-covalent N-Heterocyclic Carbene Catalysis
Ujjwal Maji1, Bhaskar Deb Mondal1, Joyram Guin1
1School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata-700032, India.
Abstract:
Herein, successful utilization of non-covalent N-heterocyclic carbene (NHC) catalysis toward asymmetric aminative dearomatization of naphthols is presented. The NHC-catalyzed process offers enantioselective synthesis of cyclic enones possessing a nitrogen-containing α-quaternary stereocenter. The reaction applies to various functionalized substrates including acid-labile groups and is shown to be scalable. Substrate activation via an O-H···NHC hydrogen-bonding interaction is suggested based on the results obtained in mechanistic studies.
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