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Synthesis of 3‐Fluoro‐3‐aryl Oxindoles: Direct Enantioselective α Arylation of Amides
Author(s) -
Wu Linglin,
Falivene Laura,
Drinkel Emma,
Grant Sharday,
Linden Anthony,
Cavallo Luigi,
Dorta Reto
Publication year - 2012
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.201200206
Subject(s) - enantioselective synthesis , carbene , ligand (biochemistry) , aryl , catalysis , combinatorial chemistry , scheme (mathematics) , chemistry , computer science , organic chemistry , mathematics , mathematical analysis , biochemistry , alkyl , receptor
Modus operandi : Catalytic access to the title compounds through a new asymmetric α‐arylation protocol is reported (see scheme). These products are formed in good yields and excellent enantioselectivities by using a new and easily synthesized chiral N‐heterocyclic carbene (NHC) ligand. Advanced DFT calculations reveal the properties of the NHC ligand and the mode of operation of the catalyst.