Photoinduced β-fragmentation of aliphatic alcohol derivatives for forging C-C bonds.
Photoinduced β-fragmentation of aliphatic alcohol derivatives for forging C-C bonds.
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DOI：
10.1038/s41467-022-35249-7
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发表时间：
2022-12-02
影响因子：
16.6
通讯作者：
Cai, Lingchao
中科院分区：
文献类型：
--
作者：
Gao, Yiman;Liu, Jie;Wei, Cong;Li, Yan;Zhang, Kui;Song, Liangliang;Cai, Lingchao
Alcohols are ubiquitous in chemistry and are native functionalities in many natural products and bioactive molecules. As such, a strategy that utilizes hydroxy-containing compounds to develop bond disconnection and bond formation process would achieve molecular diversity. Herein we utilize bench-stable N-alkoxyphthalimides prepared from alcohols to couple with glycine derivatives via radical process under visible light irradiation, providing a variety of unnatural amino acid (UAA) and peptide derivatives. The approach allows to rapidly deconstruct molecular complexity via β-fragmentation such as saclareolide, β-pinene and camphor and provides products with unique scaffolds, which show inhibition toward the pathogenic fungi growth. Transformations of alcohols, which are ubiquitous in chemistry and are native functionalities in many natural products and bioactive molecules, are cornerstones of organic synthesis. Here the authors describe photocatalyzed cross-couplings of activated alcohols with α-amino acids, providing a direct approach for a variety of unnatural amino acids.
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