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Electron-Donating and Rigid P-Stereogenic Bisphospholane Ligands for Highly Enantioselective Rhodium-Catalyzed Asymmetric Hydrogenations

Authors

  • Xiaowei Zhang,

    1. Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312
    2. Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802 (USA)
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  • Kexuan Huang,

    1. Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312
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  • Guohua Hou Dr.,

    1. Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312
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  • Bonan Cao,

    1. Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312
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  • Xumu Zhang Prof. Dr.

    1. Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312
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  • This work was supported by the National Institutes of Health (GM58832). The Bruker 400 MHz NMR spectrometer used in these studies was purchased with grant no. 1S10RR023698-01A1 from the National Center for Research Resources (NCRR), a component of the NIH. We thank Dr. T. Emge for solving the crystal structure.

Abstract

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More electron donating, more rigid: A new highly electron-donating P-stereogenic bisphospholane ligand (ZhangPhos) was synthesized in a practical and highly enantioselective manner from a commercially available chiral source. Better or comparable enantioselectivities and reactivities than TangPhos were achieved in rhodium-catalyzed hydrogenation of various functionalized olefins (see scheme; nbd=3,5-norbornadiene).

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