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Highly Enantioselective Synthesis of α-Hydroxy Phosphonic Acid Derivatives by Rh-Catalyzed Asymmetric Hydrogenation with Phosphine–Phosphoramidite Ligands

Authors

  • Dao-Yong Wang,

    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China, Fax: (+86) 411-8468-4746
    2. Graduate School of Chinese Academy of Sciences, Beijing 100039, China
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  • Xiang-Ping Hu Dr.,

    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China, Fax: (+86) 411-8468-4746
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  • Jia-Di Huang,

    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China, Fax: (+86) 411-8468-4746
    2. Graduate School of Chinese Academy of Sciences, Beijing 100039, China
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  • Jun Deng,

    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China, Fax: (+86) 411-8468-4746
    2. Graduate School of Chinese Academy of Sciences, Beijing 100039, China
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  • Sai-Bo Yu,

    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China, Fax: (+86) 411-8468-4746
    2. Graduate School of Chinese Academy of Sciences, Beijing 100039, China
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  • Zheng-Chao Duan,

    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China, Fax: (+86) 411-8468-4746
    2. Graduate School of Chinese Academy of Sciences, Beijing 100039, China
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  • Xue-Feng Xu,

    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China, Fax: (+86) 411-8468-4746
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  • Zhuo Zheng Prof. Dr.

    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China, Fax: (+86) 411-8468-4746
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  • We are grateful for the financial support from the National Natural Science Foundation of China (20472083). X.-P.H. thanks Bo Zheng and Prof. Huai-Ming Hu for solving the X-ray crystal structure.

Abstract

original image

Sehr tolerant: Unsymmetrische hybride Phosphan-Phosphoramidit-Liganden mit zentraler und axialer Chiralität wurden für die hoch enantioselektive Hydrierung verschiedenster Enolesterphosphonate genutzt (siehe Schema; cod=Cycloocta-1,5-dien). Dabei wurden für alle Klassen von β-Aryl-, β-Alkoxy- und β-Alkylsubstraten Enantioselektivitäten bis 99.9 % ee erreicht.

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