Asymmetric Ruthenium-Catalyzed Hydrogenation of 2- and 2,9-Substituted 1,10-Phenanthrolines

Authors

  • Tianli Wang,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)
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  • Fei Chen,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)
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  • Jie Qin,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)
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  • Yan-Mei He,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)
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  • Prof. Dr. Qing-Hua Fan

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)
    • Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)

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  • Financial support from the National Natural Science Foundation of China (No 21232008), National Basic Research Program of China (973 Program, 2010CB833300), and the Chinese Academy of Sciences is greatly acknowledged.

Abstract

original image

A ‘Phen'atic: The title reaction proceeds in the presence of the chiral cationic ruthenium diamine catalyst (R,R)-1 (Tf=trifluoromethanesulfonyl, Ts=4-toluenesulfonyl). Both chiral 1,2,3,4-tetrahydro- and 1,2,3,4,7,8,9,10-octahydro-1,10- phenanthroline derivatives could be obtained in high yields with excellent enantio- and diastereoselectivity.

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