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Cationic-Rhodium-Catalyzed Kinetic Resolution of Allylic Alcohols through a Redox Isomerization Reaction in a Noncoordinating Solvent

Authors

  • Kai Ren,

    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China), Fax: (+86) 21-5474-8925
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  • Lei Zhang,

    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China), Fax: (+86) 21-5474-8925
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  • Bei Hu,

    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China), Fax: (+86) 21-5474-8925
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  • Mengmeng Zhao,

    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China), Fax: (+86) 21-5474-8925
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  • Yahui Tu,

    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China), Fax: (+86) 21-5474-8925
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  • Dr. Xiaomin Xie,

    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China), Fax: (+86) 21-5474-8925
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  • Dr. Tony Y. Zhang,

    1. Chemical Product R&D, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, IN 46285-4813 (USA)
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  • Prof. Zhaoguo Zhang

    Corresponding author
    1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China), Fax: (+86) 21-5474-8925
    2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai 200032 (P.R. China)
    • School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P.R. China), Fax: (+86) 21-5474-8925
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Abstract

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On the [Rh]oad again: A series of optically pure allylic alcohols is obtained through the Rh/BINAP-catalyzed redox isomerization of racemic allylic alcohols. An improved system involves the use of cationic rhodium and a noncoordinating solvent, in which aromatic and aliphatic allylic alcohols are effectively resolved with kf/ks (kf=rate of fast reaction, ks=rate of slow reaction) values up to 24.

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