Development of ProPhenol/Ti(IV) Catalyst for Asymmetric Hydroxylative Dearomatization of Naphthols

By development of ProPhenol/Ti(IV) catalysts, a catalytic enantioselective hydroxylative dearomatization of naphthols is achieved by using TBHP as a simple oxidative reagent. The side coordinative chain equipped on the C1-position of beta- naphthols plays an important role for initiating this asymmetric hydroxylative reaction, which might be a result of the proper cocoordination effects to the titanium center in the catalyst. A reasonable catalytic cycle is proposed, the catalytic system is applied to a reasonable range of this type of phenolic compound, and related concise transformations are carried out.

Automated summary

By developing ProPhenol/Ti(IV) catalysts, a catalytic enantioselective hydroxylative dearomatization of naphthols is achieved using TBHP as a simple oxidative reagent. The side coordinative chain equipped on the C1-position of beta-naphthols plays a crucial role in initiating this asymmetric hydroxylative reaction, likely due to proper cocoordination effects to the titanium center in the catalyst. A reasonable catalytic cycle is proposed, and the catalytic system is applicable to a reasonable range of phenolic compounds of this type, enabling related concise transformations.