Asymmetric Hydrogenation of α- and β-Enamido Phosphonates: Rhodium(I)/Monodentate Phosphoramidite Catalyst

Authors

  • Dr. Jinzhu Zhang,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P.R. China)
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  • Yang Li,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P.R. China)
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  • Dr. Zheng Wang,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P.R. China)
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  • Prof. Dr. Kuiling Ding

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P.R. China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P.R. China)
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  • Financial support from the National Natural Science Foundation of China (Nos. 21172237, 20821002, 21032007), the Major Basic Research Development Program of China (Grant No. 2010CB833300), and the Chinese Academy of Sciences is gratefully acknowledged. We also thank Prof. Jiabi Chen of SIOC for his kind help in growing the single crystals of the [Rh(cod){(S,S)-L6}2]BF4 complex.

Abstract

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High efficiency and enantioselectivity have been achieved in the RhI-catalyzed asymmetric hydrogenation of α- and β-enamido phosphonates using a monophosphoramidite as the chiral ligand (see scheme; cod=1,5-cyclooctadiene), thus affording the optically active amino phosphonates with a turnover frequency of up to 1800 h−1 and high ee values.

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