Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1658-1669.DOI: 10.6023/cjoc202009048 Previous Articles     Next Articles

Original article


叶丹锋a,b, 陈浩b, 刘志园b, 雷川虎b,*()   

  1. a 上海大学材料科学与工程学院 上海 200444
    b 上海大学理学院化学系 超分子化学与催化研究中心 上海 200444
  • 收稿日期:2020-09-22 修回日期:2020-10-23 发布日期:2020-12-10
  • 通讯作者: 雷川虎
  • 基金资助:
    国家自然科学基金(21901155); 上海市青年科技启明星计划(20QA1403700); 上海高校特聘教授(东方学者)及上海大学启动基金(N.13-G210-20-263)

Transamidation of N-Benzyl-N-Boc-amides under Transition Metal-Free and Base-Free Conditions

Danfeng Yea,b, Hao Chenb, Zhiyuan Liub, Chuanhu Leib,*()   

  1. a School of Materials Science and Engineering, Shanghai University, Shanghai 200444
    b Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444
  • Received:2020-09-22 Revised:2020-10-23 Published:2020-12-10
  • Contact: Chuanhu Lei
  • About author:
    * Corresponding author. E-mail:
  • Supported by:
    National Natural Science Foundation of China(21901155); Shanghai University Startup Funding(20QA1403700); Eastern Scholars Program from the Shanghai Municipal Education Committee(N.13-G210-20-263)

A new protocol for the transamidation of N-benzyl-N-Boc-amides under transition metal-free and base-free conditions is described. The reaction features high reactivity of N-Boc-imides via direct acyl nucleophilic substitution mechanism, and provides access to a diverse array of substituted amides in good to excellent yields. Notably, the base-free condition preserves enantiopurity with respect to chiral amino-acid-derived nucleophiles, and N-Boc-amides bearing an epimerizable stereocenter. The application of this method is also demonstrated through the synthesis of pro-drugs and antidepressant moclobemide.

Key words: transamidation, N-benzyl-N-Boc-amides, transition metal-free, base-free