Abstract
A widely applicable triazole‐substituted chiral aryl iodide is described as catalyst for enantioselective oxidation reactions. The introduction of a substituent in ortho‐position to the iodide is key for its high reactivity and selectivity. Besides a robust and modular synthesis, the main advantage of this catalyst is the excellent performance in a plethora of mechanistically diverse enantioselective transformations, such as spirocyclizations, phenol dearomatizations, α‐oxygenations, and oxidative rearrangements. DFT‐calculations of in situ generated [hydroxy(tosyloxy)iodo]arene isomers give an initial rational for the observed reactivity.
Highlights
A widely applicable triazole-substituted chiral aryl iodide is described as catalyst for enantioselective oxidation reactions
Besides a robust and modular synthesis, the main advantage of this catalyst is the excellent performance in a plethora of mechanistically diverse enantioselective transformations, such as spirocyclizations, phenol dearomatizations, a-oxygenations, and oxidative rearrangements
A chiral aryl iodide precursor can be used in catalytic amounts in combination with a terminal co-oxidant to generate a chiral hypervalent iodine compound in situ
Summary
Abstract: A widely applicable triazole-substituted chiral aryl iodide is described as catalyst for enantioselective oxidation reactions. Since the discovery of the first enantioselective transformation catalyzed by a chiral aryl iodide in 2007 by Wirth and co-workers,[4] more than a dozen highly diverse C1- and C2-symmetric chiral aryl iodides have been developed.[5] Successful catalysts, such as 1–4 (Figure 1), usually show a good reactivity and selectivity in only one distinct class of oxidative transformation.
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