Design of Phosphorus Ligands with Deep Chiral Pockets: Practical Synthesis of Chiral β-Arylamines by Asymmetric Hydrogenation

Authors

  • Dr. Guodu Liu,

    1. State Key Laboratory of Bio-organic and Natural Products, Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai 200032 (China)
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  • Xiangqian Liu,

    1. State Key Laboratory of Bio-organic and Natural Products, Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai 200032 (China)
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  • Zhihua Cai,

    1. State Key Laboratory of Bio-organic and Natural Products, Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai 200032 (China)
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  • Guangjun Jiao,

    1. State Key Laboratory of Bio-organic and Natural Products, Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai 200032 (China)
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  • Guangqing Xu,

    1. State Key Laboratory of Bio-organic and Natural Products, Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai 200032 (China)
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  • Prof. Dr. Wenjun Tang

    Corresponding author
    1. State Key Laboratory of Bio-organic and Natural Products, Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai 200032 (China)
    • State Key Laboratory of Bio-organic and Natural Products, Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai 200032 (China)
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  • We are grateful to NSFC-21272254, the “Thousand Plan” Youth program, State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, and Boehringer Ingelheim.

Abstract

original image

WingPhos, ein C2-symmetrischer Bisphosphorligand mit einer tiefen und definierten chiralen Tasche, wurde in der Rhodium-katalysierten asymmetrischen Hydrierung von (E)-β-Aryl-N-acetylenamiden, cyclischen β-Arylenamiden und heterocyclischen β-Arylenamiden eingesetzt. Chirale β-Arylisopropylamine, 2-Aminotetraline und 3-Aminochromane können mit ausgezeichneten ee-Werten synthetisiert werden (nbd=3,5-Norbornadien; TON=Umsatzzahl).

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