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Recent advances in the synthesis of N-heterocycles from α-amino acids mediated by iodine
Chemical Communications ( IF 4.3 ) Pub Date : 2024-11-14 , DOI: 10.1039/d4cc05285d Dong-Sheng Yang, Jia-Chen Xiang, An-Xin Wu
Chemical Communications ( IF 4.3 ) Pub Date : 2024-11-14 , DOI: 10.1039/d4cc05285d Dong-Sheng Yang, Jia-Chen Xiang, An-Xin Wu
The synthesis of N-heterocycles has received extensive attention from scientists considering their important role in organic synthesis, pharmaceuticals, and materials chemistry. α-Amino acids (α-AAs), both natural and non-natural, are structurally diverse, containing basic amino groups, acidic carboxyl groups, and various side-chain R groups in a single molecule. Given their structural properties and wide range of sources, they have undoubtedly become suitable synthetic building blocks for organic synthesis. However, conventional transformations of amino acids (AAs) focus on the amino and carboxyl groups independently. Conversions for these two prominent functional groups generally do not affect both their alpha positions and their branched chains. Over the past decade, with the application of iodine (I2) in the field of heterocyclic synthesis, the use of α-AAs for diverse construction of complex N-heterocyclic structures has gained increasing attention. This synthetic strategy relies on the I2-mediated Strecker degradation, which introduces α-AAs as electrophilic carbon species into the domino reaction sequence via decarboxylation and deamination processes. In this review, we have summarized recent advances in this emerging area.
中文翻译:
碘介导的 α-氨基酸合成 N-杂环的研究进展
考虑到 N-杂环在有机合成、制药和材料化学中的重要作用,N-杂环的合成受到了科学家的广泛关注。天然和非天然的 α-氨基酸 (α-AA) 在结构上是多种多样的,在单个分子中包含碱性氨基、酸性羧基和各种侧链 R 基团。鉴于它们的结构特性和广泛的来源,它们无疑已成为有机合成的合适合成构件。然而,氨基酸 (AA) 的常规转化独立地集中在氨基和羧基上。这两个突出官能团的转换通常不会影响它们的 α 位置和支链。近十年来,随着碘 (I2) 在杂环合成领域的应用,α-AAs 在复杂 N-杂环结构的多样化构建中的应用越来越受到关注。这种合成策略依赖于 I2 介导的 Strecker 降解,该降解通过脱羧和脱氨过程将 α-AA 作为亲电碳物质引入多米诺反应序列中。在这篇综述中,我们总结了这一新兴领域的最新进展。
更新日期:2024-11-14
中文翻译:
碘介导的 α-氨基酸合成 N-杂环的研究进展
考虑到 N-杂环在有机合成、制药和材料化学中的重要作用,N-杂环的合成受到了科学家的广泛关注。天然和非天然的 α-氨基酸 (α-AA) 在结构上是多种多样的,在单个分子中包含碱性氨基、酸性羧基和各种侧链 R 基团。鉴于它们的结构特性和广泛的来源,它们无疑已成为有机合成的合适合成构件。然而,氨基酸 (AA) 的常规转化独立地集中在氨基和羧基上。这两个突出官能团的转换通常不会影响它们的 α 位置和支链。近十年来,随着碘 (I2) 在杂环合成领域的应用,α-AAs 在复杂 N-杂环结构的多样化构建中的应用越来越受到关注。这种合成策略依赖于 I2 介导的 Strecker 降解,该降解通过脱羧和脱氨过程将 α-AA 作为亲电碳物质引入多米诺反应序列中。在这篇综述中,我们总结了这一新兴领域的最新进展。