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Rhodium‐Catalyzed Enantioselective Reductive Arylation: Convenient Access to 3,3‐Disubstituted Oxindoles
Author(s) -
Jang Young Jin,
Larin Egor M.,
Lautens Mark
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.201704922
Subject(s) - rhodium , enantioselective synthesis , catalysis , chemistry , intramolecular force , combinatorial chemistry , reactivity (psychology) , organic chemistry , medicine , alternative medicine , pathology
Abstract A rhodium‐Josiphos(L*) catalyzed enantioselective intramolecular hydroarylation reaction is described. The reductive cyclization of o ‐bromoaniline‐derived acrylamides provides convenient access to 3,3‐disubstituted oxindoles in good yields and with excellent enantioselectivity across a range of substrates. We propose that the key cyclization proceeds via a rhodium(III) intermediate. Overall, this method represents an unusual mode of reactivity for rhodium catalysis and is complementary to palladium(0)‐catalyzed α‐arylation methods.