Asymmetric Adler-Becker reaction - an open issue

The Adler-Becker reaction, described in the 1970s, plays a crucial role in the total synthesis of numerous natural products. This reaction describes the transformation of salicylic alcohols into spiroepoxydienones through oxidative dearomatization. Despite its widespread use, the literature lacks a description of the chiral version of this reaction. In this study, we detail several attempts to achieve asymmetry, utilizing a biphasic solvent system with various potential chiral phase transfer catalysts (including chinchonine and sparteine). Additionally, we explored periodate salts with chiral cations and sodium periodate immobilized in a chiral cationic resin. Although the desired enantioselectivity remained elusive, we believe that this work can contribute to the scientific community, as it can serve as a guiding reference for exploring novel chiral approaches in this reaction.