Get access

Interplay of Direct Stereocontrol and Dynamic Kinetic Resolution in a Bifunctional Amine Thiourea Catalyzed Highly Enantioselective Cascade Michael–Michael Reaction

Authors

  • Chenguang Yu,

    1. Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA), Fax: (+1) 505-277-2609
    2. State Key Laboratory of Chemical Resources Engineering, Beijing University of Chemical Technology, Beijing 100029 (P. R. China)
    Search for more papers by this author
  • Dr. Yinan Zhang,

    1. Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA), Fax: (+1) 505-277-2609
    Search for more papers by this author
  • Aiguo Song,

    1. Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA), Fax: (+1) 505-277-2609
    Search for more papers by this author
  • Prof. Dr. Yafei Ji,

    Corresponding author
    1. Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA), Fax: (+1) 505-277-2609
    2. School of Pharmacy, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237 (P. R. China)
    • Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA), Fax: (+1) 505-277-2609
    Search for more papers by this author
  • Prof. Dr. Wei Wang

    Corresponding author
    1. Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA), Fax: (+1) 505-277-2609
    2. School of Pharmacy, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237 (P. R. China)
    3. Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203 (P. R. China)
    • Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA), Fax: (+1) 505-277-2609
    Search for more papers by this author

Abstract

original image

Control is better: A novel chiral amine thiourea catalyzed, highly enantioselective Michael–Michael cascade process serves as a “one-pot” approach to synthetically and biologically significant chiral tetrahydrothiophenes (see scheme). Notably, an unprecedented cooperative direct stereocontrol and dynamic kinetic resolution by the bifunctional catalyst is identified that governs the highly enantioselective cascade process.

Get access to the full text of this article

Ancillary