The successful development of the classical Pinnick oxidation into a new and promising oxidative lactonization reaction is reported. Chiral 3-oxindolepropionic aldehydes, Michael adducts of 3-olefinic oxindoles with aliphatic aldehydes, are directly converted to spirocyclic oxindole-γ-lactones solely by sodium chlorite via a tandem Pinnick oxidation/chlorination/substitution sequence. This reaction uses waste ClO generated in the initial Pinnick oxidation as an ecofriendly halogenating agent for the subsequent chlorination, and then it utilizes the byproduct OH formed in the chlorination to facilitate the final internal substitution.

An unprecedented and challenging simultaneous carboxylation/halogenation, and next lactonization of γ,γ-dicarbonyl-substituted aldehydes has been realized using a NaClO2/DBDMH combination.

By merging organocatalysis with copper catalysis, a highly efficient stereospecific approach for the synthesis of chiral phenols from cyclohexanones has been developed for the first time. The aromatization reaction proceeds through the in situ formation of enone intermediates and further subsequent bromination/dehydrobromination reactions. And a series of functionalized phenol derivatives are obtained in good yields (up to 89%) and good to excellent enantioselectivities (up to 99% ee).