Chinese Journal of Organic Chemistry >
Transamidation of N-Benzyl-N-Boc-amides under Transition Metal-Free and Base-Free Conditions
Received date: 2020-09-22
Revised date: 2020-10-23
Online published: 2020-12-10
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
Danfeng Ye , Hao Chen , Zhiyuan Liu , Chuanhu Lei . Transamidation of N-Benzyl-N-Boc-amides under Transition Metal-Free and Base-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2021 , 41(4) : 1658 -1669 . DOI: 10.6023/cjoc202009048
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