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Asymmetric Synthesis of Isoindolones by Chiral Cyclopentadienyl‐Rhodium(III)‐Catalyzed CH Functionalizations
Author(s) -
Ye Baihua,
Cramer Nicolai
Publication year - 2014
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.201404895
Subject(s) - cyclopentadienyl complex , rhodium , chemistry , diazo , catalysis , ligand (biochemistry) , alkyl , asymmetric hydrogenation , enantioselective synthesis , combinatorial chemistry , asymmetric carbon , selectivity , acceptor , stereochemistry , organic chemistry , biochemistry , receptor , physics , condensed matter physics
Directed Cp*Rh III ‐catalyzed carbon–hydrogen (CH) bond functionalizations have evolved as a powerful strategy for the construction of heterocycles. Despite their high value, the development of related asymmetric reactions is largely lagging behind due to a limited availability of robust and tunable chiral cyclopentadienyl ligands. Rhodium complexes comprising a chiral Cp ligand with an atropchiral biaryl backbone enables an asymmetric synthesis of isoindolones from arylhydroxamates and weakly alkyl donor/acceptor diazo derivatives as one‐carbon component under mild conditions. The complex guides the substrates with a high double facial selectivity yielding the chiral isoindolones in good yields and excellent enantioselectivities.