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Abstract
As part of our investigations into C-C bond scission and functionalization, we report a halodealkenylation in which the C(sp3)-C(sp2) bonds of alkenes are cleaved and C(sp3)-halide bonds are formed, via a radical intermediate. These transformations occur through Criegee ozonolysis and FeII-catalyzed reductive coupling assisted by vitamin C as a stoichiometric reductant. We applied this strategy to the formal synthesis of (R,R,R)-γ-tocopherol.
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