Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 32, Pages 12433-12438Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c04773
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Funding
- NSFC [21922107, 21772171]
- Zhejiang Provincial Natural Science Foundation of China [LR19B020001]
- Center of Chemistry for Frontier Technologies
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This study presents an iron-catalyzed highly enantioselective hydrogenation method for the synthesis of chiral alkanes from minimally functionalized 1,1-disubstituted alkenes. A novel chiral 8-oxazoline iminoquinoline ligand and its iron complex have been designed and synthesized to facilitate this transformation. The reaction is operationally simple, utilizing 1 atm of hydrogen gas, and demonstrates good functional group tolerance.
Here, we reported for the first time an iron-catalyzed highly enantioselective hydrogenation of minimally functionalized 1,1-disubstituted alkenes to access chiral alkanes with full conversion and excellent ee. A novel chiral 8-oxazoline iminoquinoline ligand and its iron complex have been designed and synthesized. This protocol is operationally simple by using 1 atm of hydrogen gas and shows good functional group tolerance. A primary mechanism has been proposed by the deuterium-labeling experiments.
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