Aqueous Flavin Photoredox Catalysis Drives Exclusive C3-Alkylation of Indolyl Radical Cations in Route to Unnatural Tryptophan Mimetics.
Aqueous Flavin Photoredox Catalysis Drives Exclusive C3-Alkylation of Indolyl Radical Cations in Route to Unnatural Tryptophan Mimetics.
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DOI：
10.1021/acs.orglett.3c01398
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发表时间：
2023-05
期刊：
影响因子：
5.2
通讯作者：
Jacob R. Immel;Bayan M Alghafli;Allen Alonso Rodríguez Ugalde;Steven Bloom
中科院分区：
文献类型：
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作者：
Jacob R. Immel;Bayan M Alghafli;Allen Alonso Rodríguez Ugalde;Steven Bloom
建立吲哚化学多样性的一种方法是将它们氧化成吲哚基阳离子（Ind•+）。这些中间体可以在C2- c3键上接受新的官能团，也可以在C2上独立接受新的官能团。较少遇到的是C3的选择性多样化，这是一个受竞争性脱芳香副反应困扰的位置。我们公开了一种水光氧化催化将Ind•+转化为C3取代色氨酸模拟物的方法，该方法使用水作为瞬时保护基团来指导C3选择性烷基化。
One way to build chemical diversity into indoles is to oxidize them to indolyl radical cations (Ind•+). These intermediates can accept new functional groups across C2-C3 bonds or independently at C2. Less encountered is selective diversification at C3, a position plagued by competing dearomative side reactions. We disclose an aqueous photoredox-catalyzed method for transforming Ind•+ into C3-substituted tryptophan mimetics that uses water as a transient protecting group to guide site-selective C3 alkylation.