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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

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WingPhos, a C2-symmetric bisphosphorus ligand with a deep and well-defined chiral pocket was developed. It has shown high efficiency in the rhodium-catalyzed asymmetric hydrogenation of (E)-β-aryl-N-acetyl enamides, cyclic β-aryl enamides, and heterocyclic β-aryl enamides. A series of chiral β-arylisopropylamines, 2-aminotetralines, and 3-aminochromans can be synthesized with excellent ee values (nbd=3,5-norbornadiene; TON=turnover number).

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