Enantioselective Synthesis of Aza-Flavanones with an All-Carbon Quaternary Stereocenter via NHC-Catalyzed Intramolecular Annulation

Izabela Barańska; Michał Słotwiński; Tadeusz Muzioł; Zbigniew Rafiński

doi:10.1021/acsomega.3c05064

Enantioselective Synthesis of Aza-Flavanones with an All-Carbon Quaternary Stereocenter via NHC-Catalyzed Intramolecular Annulation

ACS Omega. 2023 Oct 30;8(44):41480-41484. doi: 10.1021/acsomega.3c05064. eCollection 2023 Nov 7.

Authors

Izabela Barańska¹, Michał Słotwiński¹, Tadeusz Muzioł¹, Zbigniew Rafiński¹

Affiliation

¹ Faculty of Chemistry, Nicolaus Copernicus University in Torun, 7 Gagarin Street, 87-100 Torun, Poland.

Abstract

An enantioselective synthesis of functionalized aza-flavanone derivatives using the N-heterocyclic carbene-catalyzed intramolecular Stetter reaction of sulphoamido benzaldehydes has been reported. This procedure presents the first original approach for synthesizing chiral functionalized flavonoids at the 3-position, containing an all-carbon quaternary stereogenic center. This advancement significantly enriches the chemical toolbox for the preparation of complex nitrogen-containing compounds and opens up new avenues for further research and development in synthetic organic chemistry.