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Asymmetric Hydrogenation of Quinoxalines with Diphosphinite Ligands: A Practical Synthesis of Enantioenriched, Substituted Tetrahydroquinoxalines

Authors

  • Weijun Tang Dr.,

    1. Department of Applied Biology and Chemical Technology and Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The Hong Kong Polytechnic University, Hong Kong (China)
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  • Lijin Xu Prof.,

    1. Department of Chemistry, Renmin University of China, Beijing 100872 (China)
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  • Qing-Hua Fan Prof.,

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

    1. Department of Applied Biology and Chemical Technology and Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The Hong Kong Polytechnic University, Hong Kong (China)
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  • Baomin Fan Dr.,

    1. Department of Applied Biology and Chemical Technology and Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The Hong Kong Polytechnic University, Hong Kong (China)
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  • Zhongyuan Zhou Prof.,

    1. Department of Applied Biology and Chemical Technology and Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The Hong Kong Polytechnic University, Hong Kong (China)
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  • Kim-hung Lam Dr.,

    1. Department of Applied Biology and Chemical Technology and Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The Hong Kong Polytechnic University, Hong Kong (China)
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  • Albert S. C. Chan Prof.

    1. Department of Applied Biology and Chemical Technology and Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The Hong Kong Polytechnic University, Hong Kong (China)
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  • Financial support from the Hong Kong Research Grants Council (Polyu 5001/07P), the Hong Kong UGC AoE Scheme (AoE P/10-01), the Hong Kong Polytechnic University Areas of Strategic Development Fund, the National Natural Science Foundation of China (20873179, 20532010), the Ministry of Science and Technology (nos. 2007CB935904 and 2010CB833305), the Renmin University of China, and the Chinese Academy of Sciences is greatly acknowledged.

Abstract

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An easily accessible chiral Ir/H8-binapo catalyst exhibits unprecedented reactivity and excellent enantioselectivity in the hydrogenation of quinoxalines at a high ratio of substrate to catalyst (from 100 to 20 000). This new method provides a practical synthetic approach to give optically active chiral tetrahydroquinoxaline derivatives (see scheme; cod=1,5-cyclooctadiene).

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