Dirhodium Carboxylates Catalyzed Enantioselective Coupling Reactions of α-Diazophosphonates, Anilines, and Electron-Deficient Aldehydes

Authors

  • Cong-Ying Zhou,

    1. Department of Chemistry, State Key Laboratory of Synthetic Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, University of Hong Kong, Pokfulam Road (Hong Kong, China)
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    • These authors contributed equally to this work.

  • Jing-Cui Wang,

    1. Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 354 Feng Lin Road, Shanghai (China)
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    • These authors contributed equally to this work.

  • Jinhu Wei,

    1. Department of Chemistry, State Key Laboratory of Synthetic Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, University of Hong Kong, Pokfulam Road (Hong Kong, China)
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  • Zhen-Jiang Xu,

    1. Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 354 Feng Lin Road, Shanghai (China)
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  • Zhen Guo,

    1. Department of Chemistry, State Key Laboratory of Synthetic Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, University of Hong Kong, Pokfulam Road (Hong Kong, China)
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  • Kam-Hung Low,

    1. Department of Chemistry, State Key Laboratory of Synthetic Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, University of Hong Kong, Pokfulam Road (Hong Kong, China)
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  • Prof. Dr. Chi-Ming Che

    Corresponding author
    1. Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 354 Feng Lin Road, Shanghai (China)
    • Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 354 Feng Lin Road, Shanghai (China)
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  • We are thankful for financial support from the University of Hong Kong (University Development Fund), Hong Kong Research Grants Council (HKU 700708P, HKU1/CRF/08), CAS-GJHZ200816 and CAS-Croucher Funding Scheme for Joint Laboratory, and the Areas of Excellence Scheme established under the University Grants Committee of the Hong Kong Special Administrative Region, China (AoE/P- 10/01). We thank Chen Yang (HKU) for the X-ray crystallographic structural determination.

Abstract

original image

Chiral dirhodium carboxylate complexes ([Rh2(S-PTAD)4] or [Rh2(S-PTTL)4], see scheme) efficiently catalyze asymmetric three-component coupling reactions of α-diazophosphonates, anilines, and electron-deficient aldehydes to give α-amino-β-hydroxyphosphonates. The high level of enantiocontrol provides evidence for the intermediacy of metal-bound ammonium ylide in the product-forming step.

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