Get access

Enantioselective Decarboxylative Amination: Synthesis of Axially Chiral Allenyl Amines

Authors

  • Baoqiang Wan,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai, Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
    Search for more papers by this author
  • Prof. Dr. Shengming Ma

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai, Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
    2. Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062 (P.R. China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai, Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)

    Search for more papers by this author

  • Financial support from the National Natural Science Foundation of China (21232006) and the Major State Basic Research and Development Program (2011CB808700) is greatly appreciated. We thank Minyan Wang from our research group for reproducing the results for compounds 2 i, (S)-2 d, and (S)-2 v.

Abstract

original image

Getting axed: Synthesis of the title amines, bearing functionality (R1 and R2), involves the enantioselective palladium-catalyzed decarboxylation of allenyl N-tosylcarbamates. The reaction proceeds smoothly using both the chiral ligands (S)- and (R)-DTBM-Segphos (1) to afford the allenyl amines in good yields and with high enantioseletivities.

Get access to the full text of this article

Ancillary