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

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.

SUBMITTER: Baranska I

PROVIDER: S-EPMC10633870 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

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

Barańska Izabela I Słotwiński Michał M Muzioł Tadeusz T Rafiński Zbigniew Z

ACS omega 20231030 44

An enantioselective synthesis of functionalized <i>aza</i>-flavanone derivatives using the <i>N</i>-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 ...[more]

PMID: 37969996

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