Journal
ORGANIC LETTERS
Volume 20, Issue 3, Pages 808-811Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03948
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A kinetic study on the reactions of the cumyloxyl radical (CumO(center dot)) 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 alpha-C-H bonds activating these bonds toward HAT to the electrophilic CumO(center dot) 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.
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