Photocatalytic Three-Component Umpolung Synthesis of 1,3-Diamines.
Photocatalytic Three-Component Umpolung Synthesis of 1,3-Diamines.
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DOI：
10.1021/acs.orglett.8b02923
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发表时间：
2018-10
期刊：
影响因子：
5.2
通讯作者：
Thomas Rossolini;Jamie A. Leitch;Rachel Grainger;D. Dixon
中科院分区：
文献类型：
--
作者：
Thomas Rossolini;Jamie A. Leitch;Rachel Grainger;D. Dixon
描述了从原位生成的亚胺和脱氢丙氨酸衍生物中可见光介导的光催化反相合成 1,3-二胺。这种三组分偶联反应以光催化产生的 α-氨基自由基与缺电子烯烃的关键亲核加成为中心，有效且非对映选择性地提供 1,3-二胺。温和的方案可耐受多种功能，包括杂环、频哪醇硼酸酯和脂肪链。还证明了其在生物学相关的 α-氨基-γ-内酰胺合成和扩展到 1,3-氨基醇中的应用。
A visible-light-mediated photocatalytic umpolung synthesis of 1,3-diamines from in situ-generated imines and dehydroalanine derivatives is described. Pivoting on a key nucleophilic addition of photocatalytically generated α-amino radicals to electron-deficient alkenes, this three-component coupling reaction affords 1,3-diamines efficiently and diastereoselectively. The mild protocol tolerates a wide variety of functionalities including heterocycles, pinacol boronates, and aliphatic chains. Application to biologically relevant α-amino-γ-lactam synthesis and extension to 1,3-aminoalcohols is also demonstrated.