Metal-free dearomatization reactions of naphthol-ynamides for the divergent and enantioselective synthesis of azaspirocycles

Dearomatization reactions of phenols and their derivatives have evolved as efficient and practical methods for the synthesis of functionalized spirocyclic enones in the past decades. Here, an efficient metal-free intramolecular dearomatization cyclization of readily available naphthol-ynamides has been developed, enabling practical, atom-economical and divergent access to two azaspirocyclic compounds in mostly good to excellent yields with a wide substrate scope. Moreover, such a catalytic asymmetric dearomatization reaction has also been achieved by employing a chiral Bronsted acid as a catalyst.

Automated summary

Efficient metal-free dearomatization cyclization of naphthol-ynamides has been developed, allowing for the practical synthesis of two azaspirocyclic compounds. Additionally, catalytic asymmetric dearomatization reaction has also been achieved using a chiral Bronsted acid catalyst.