Iridium-Catalyzed Asymmetric Hydrogenation of Pyridinium Salts†
Zhi-Shi Ye
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/
Search for more papers by this authorMu-Wang Chen
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/
Search for more papers by this authorQing-An Chen
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/
Search for more papers by this authorLei Shi
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/
Search for more papers by this authorYing Duan
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/
Search for more papers by this authorCorresponding Author
Prof. Yong-Gui Zhou
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/Search for more papers by this authorZhi-Shi Ye
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/
Search for more papers by this authorMu-Wang Chen
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/
Search for more papers by this authorQing-An Chen
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/
Search for more papers by this authorLei Shi
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/
Search for more papers by this authorYing Duan
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/
Search for more papers by this authorCorresponding Author
Prof. Yong-Gui Zhou
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian 116023 (China) http://www.lac.dicp.ac.cn/Search for more papers by this authorFinancial support was provided by the National Natural Science Foundation of China (21032003, 20921092 and 21125208) and the National Basic Research Program of China (2010CB833300).
Graphical Abstract
Highly efficient iridium-catalyzed asymmetric hydrogenations of simple 2-substituted pyridinium salts gives the chiral 2-substituted piperidines with up to 93 % ee (see picture; cod=1,5-cyclooctadiene; synphos=(5,6),(5′,6′)-bis(ethylenedioxy)-2,2′-bis(diphenylphosphino)-1,1′-biphenyl). The key feature of this strategy is the activation of simple pyridines as the pyridinium salts, thus eliminating substrate inhibition and enhancing the reactivity.
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