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Chiral Phase‐Transfer‐Catalyzed Intramolecular aza‐Michael Reactions for the Asymmetric Synthesis of Isoindolinones
Author(s) -
Lebrun Stéphane,
Sallio Romain,
Dubois Mélanie,
AgbossouNiedercorn Francine,
Deniau Eric,
Michon Christophe
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403573
Subject(s) - intramolecular force , benzamide , chemistry , michael reaction , catalysis , optically active , combinatorial chemistry , intramolecular reaction , enantioselective synthesis , stereochemistry , organic chemistry
Asymmetric intramolecular aza‐Michael reactions catalyzed by cinchoninium phase‐transfer organocatalysts are used for the synthesis of optically active isoindolinones. Selected oligomeric cinchoninium salts are efficient and selective catalysts for the intramolecular addition of alkenylated benzamide substrates. The resulting compounds are useful intermediates for the synthesis and development of benzodiazepine‐receptor agonists.