Get access

A Strategy Enabling Enantioselective Direct Conjugate Addition of Inert Aryl Methane Nucleophiles to Enals with a Chiral Amine Catalyst under Mild Conditions

Authors

  • Tengfei Li,

    1. Shanghai Key Laboratory of New Drug Design, School of Pharmacy and State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-6425-2584
    Search for more papers by this author
  • Dr. Jin Zhu,

    1. Shanghai Key Laboratory of New Drug Design, School of Pharmacy and State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-6425-2584
    Search for more papers by this author
  • Deyan Wu,

    1. Shanghai Key Laboratory of New Drug Design, School of Pharmacy and State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-6425-2584
    Search for more papers by this author
  • Xiangmin Li,

    1. Shanghai Key Laboratory of New Drug Design, School of Pharmacy and State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-6425-2584
    Search for more papers by this author
  • Sinan Wang,

    1. Shanghai Key Laboratory of New Drug Design, School of Pharmacy and State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-6425-2584
    Search for more papers by this author
  • Prof. Dr. Hao Li,

    1. Shanghai Key Laboratory of New Drug Design, School of Pharmacy and State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-6425-2584
    Search for more papers by this author
  • Prof. Dr. Jian Li,

    Corresponding author
    1. Shanghai Key Laboratory of New Drug Design, School of Pharmacy and State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-6425-2584
    • Shanghai Key Laboratory of New Drug Design, School of Pharmacy and State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-6425-2584
    Search for more papers by this author
  • Prof. Dr. Wei Wang

    Corresponding author
    1. Shanghai Key Laboratory of New Drug Design, School of Pharmacy and State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-6425-2584
    2. Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA), Fax: (+1) 505-277-2609
    • Shanghai Key Laboratory of New Drug Design, School of Pharmacy and State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237 (P.R. China), Fax: (+86) 21-6425-2584
    Search for more papers by this author

Abstract

original image

Nitro-charged activation: An organocatalytic enantioselective conjugate addition of aryl methyl nucleophiles to enals has been developed to produce ubiquitous chiral benzylic building blocks (see scheme; TES=triethylsilyl). Taking advantage of the strongly electron-withdrawing nature of nitro groups, which can be conveniently transformed into other functionalities, this functionality was incorporated into aromatic systems as a temporary activating group.

Get access to the full text of this article

Ancillary