Synthesis of α-Amino Tertiary Alkylperoxides by Lewis Acid-Catalyzed Peroxidation of 1,3,5-Triazines

Lijuan Liu; Zhichao Shi; Xun Zhang; Feng Zhan; Jin-Shun Lin; Yuyang Jiang

doi:10.1002/asia.202100833

Synthesis of α-Amino Tertiary Alkylperoxides by Lewis Acid-Catalyzed Peroxidation of 1,3,5-Triazines

Chem Asian J. 2021 Nov 2;16(21):3487-3491. doi: 10.1002/asia.202100833. Epub 2021 Sep 16.

Authors

Lijuan Liu^{1

2}, Zhichao Shi^{2

3

4

5}, Xun Zhang^{2

6}, Feng Zhan², Jin-Shun Lin^{2

6}, Yuyang Jiang^{2

3

7}

Affiliations

¹ Department of Chemical Engineering, Tsinghua University, Beijing, 100084, P. R. China.
² The State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Biology, Tsinghua Shenzhen International Graduate School, Tsinghua University, Shenzhen, 518055, P. R. China.
³ Institute of Biomedical Health Technology and Engineering, Shenzhen Bay Laboratory, Shenzhen, 518132, P. R. China.
⁴ National & Local United Engineering Lab for Personalized Anti-tumor Drugs, Shenzhen Kivita Innovative Drug Discovery Institute, Tsinghua Shenzhen International Graduate School, Shenzhen, 518055, P. R. China.
⁵ College of Pharmacy, Jinan University, Guangzhou, 510632, P. R. China.
⁶ Department of Chemistry, Tsinghua University, Beijing, 100084, P. R. China.
⁷ Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, 100084, P. R. China.

PMID: 34478220
DOI: 10.1002/asia.202100833

Abstract

α-Substituted peroxides have been found in natural products and are widely used as anti-malarial agents. Zn(OTf)₂ -catalyzed peroxidation of 1,3,5-triazines has been developed, accessing diversely substituted α-amino tertiary alkylperoxides with high efficiency. Mechanistic investigations and useful synthetic application of the products have also been presented.

Keywords: 1,3,5-triazines; Lewis acid; peroxidation; α-amino tertiary alkylperoxides.

Abstract

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