期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 47, 页码 16831-16834出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201909919
关键词
asymmetric hydrogenation; N-heterocyclic carbenes; reductive amination; tandem reactions; vicinal diamines
资金
- National Natural Science Foundation of China [21790332, 21521002, 21772204]
- CAS [QYZDJSSW-SLH023]
A highly enantioselective iridium- or ruthenium-catalyzed intermolecular reductive amination/asymmetric hydrogenation relay with 2-quinoline aldehydes and aromatic amines has been developed. A broad range of sterically tunable chiral N,N'-diaryl vicinal diamines were obtained in high yields (up to 95%) with excellent enantioselectivity (up to >99% ee). The resulting chiral diamines could be readily transformed into sterically hindered chiral N-heterocyclic carbene (NHC) precursors, which are otherwise difficult to access. The usefulness of this synthetic approach was further demonstrated by the successful application of one of the chiral vicinal diamines and chiral NHC ligands in a transition-metal-catalyzed asymmetric Suzuki-Miyaura cross-coupling reaction and asymmetric ring-opening cross-metathesis, respectively.
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