Work

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

Year: 2021

Type: article

Abstract: 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.

Source: Chinese Journal of Organic Chemistry

DOI: 10.6023/cjoc202009048

Authors: Danfeng Ye, Hao Chen, Zhiyuan Liu, Chuanhu Lei

Institution: Shanghai University

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Natural Science Foundation of China, Shanghai Rising-Star Program

Awards: G1943961179, G2827633932