Enhancing Reactivity and Site-Selectivity in Hydrogen Atom Transfer from Amino Acid C–H Bonds via Deprotonation,Organic Letters

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Enhancing Reactivity and Site-Selectivity in Hydrogen Atom Transfer from Amino Acid C–H Bonds via Deprotonation
Organic Letters ( IF 4.9 ) Pub Date : 2018-01-12 00:00:00 , DOI: 10.1021/acs.orglett.7b03948
Luca Maria Pipitone ₁ , Giulia Carboni ₁ , Daniela Sorrentino ₁ , Marco Galeotti ₁ , Michela Salamone ₁ , Massimo Bietti ₁

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A kinetic study on the reactions of the cumyloxyl radical (CumO^•) with N-Boc-protected amino acids in the presence of the strong organic base DBU has been carried out. CO₂H deprotonation increases the electron density at the α-C–H bonds activating these bonds toward HAT to the electrophilic CumO^• strongly influencing the intramolecular selectivity. The implications of these results are discussed in the framework of HAT-based aliphatic C–H bond functionalization of amino acids and peptides.

中文翻译：

通过去质子化从氨基酸C–H键转移氢原子的反应性和位点选择性

在强有机碱DBU的存在下，对枯草酰氧基（CumO ^•）与N - Boc保护的氨基酸的反应进行了动力学研究。CO ₂ H去质子化增加了α-C–H键上的电子密度，从而激活了这些键对HAT的亲电性CumO ^•，极大地影响了分子内的选择性。这些结果的含义在基于HAT的氨基酸和肽的脂肪族C–H键功能化框架中进行了讨论。

更新日期：2018-01-12

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