ZIOC scientists developed an asymmetric method for the synthesis of aminochromone derivatives

Chromones and flavonoids are natural compounds that exhibit various bioactivities, including anticancer, antibacterial, and antifungal properties. Student of the Nazarov Laboratory of Fine Organic Synthesis of the Zelinsky Institute Ruslan Kovalevsky and co-authors developed an enantioselective method for obtaining various chiral alpha-amino-containing chromones and their derivatives. The key stage of the synthesis proceeded through the asymmetric addition of 3-hydroxychromones to N-protected imines (Mannich reaction) in the presence of the natural dihydrocupreine alkaloid (2-5 mol%) as an organocatalyst. The proposed approach can be extended to obtain a large number of aminochromones with high enantioselectivity (89-98% ee). The resulting compounds can be further used as intermediates for the synthesis of polyfunctional substrates.

The research was supported by the Russian Science Foundation (Grant No. 23-13-00250).

Source:

Ruslan A. Kovalevsky, Konstantin V. Vasechkin, Alexander S. Kucherenko, Sergei G. Zlotin Enantioselective Catalytic Synthesis of α-Stereogenic Chromen-4-one Amino Derivatives // Adv. Synth. Catal., 2023, accepted manuscript. DOI: 10.1002/adsc.202300659.