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Updated: Jun 8, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
Ruthenium-Catalyzed Solvent-Controlled Chemoselective Asymmetric Hydrogenation of 2,8'-Bisquinoline Derivatives
Yi Yang1,2, Shu-Xin Zhang1, Qingduan Meng1,2
1Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
None:
We report the first solvent-controlled chemoselective asymmetric hydrogenation of 2,8'-bisquinolines using chiral Ru/N-sulfonylated diamine complexes. By simply switching the solvent from dichloromethane to methanol, either chiral 1',2',3',4'-tetrahydrobisquinolines or 1,1',2,2',3,3',4,4'-octahydrobisquinolines were obtained in high yields with excellent enantioselectivities. The methodology was successfully applied to scale-up syntheses and the preparation of a new C1-symmetric N-heterocyclic carbene ligand. Preliminary mechanistic study revealed that an intramolecular hydrogen bond in the tetrahydroquinoline intermediate is the key factor governing the chemoselectivity, which can be disrupted in protic solvents.
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