New advances in asymmetric organocatalysis

• Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 240–242, doi:10.3762/bjoc.18.28

• type of Brønsted acid catalyst that expanded the range of available acidities as well as molecular arrangements in acid-catalyzed reactions. Veselý and co-workers demonstrated that these catalysts are effective in the enantioselective aminalization of aldehydes with anthranilamides [24]. To explore new

Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes

• Martin Kamlar,
• Robert Reiberger,
• Martin Nigríni,
• Ivana Císařová and
• Jan Veselý

Beilstein J. Org. Chem. 2021, 17, 2433–2440, doi:10.3762/bjoc.17.160

• Abstract Here we present an enantioselective aminalization of aldehydes catalyzed by Brønsted acids based on pentacarboxycyclopentadienes (PCCPs). The cyclization reaction using readily available anthranilamides as building blocks provides access to valuable 2,3-dihydroquinazolinones containing one

• stereogenic carbon center with good enantioselectivity (ee up to 80%) and excellent yields (up to 97%). Keywords: aminalization; Brønsted acid; organocatalysis; PCCP; pentacarboxycyclopentadiene; Introduction Nitrogen-containing heterocyclic compounds are commonly occurring in nature and constitute the core

• corresponding dihydroquinazolinones were obtained in high yields and with good enantiomeric purities. In 2013, Lin and co-workers published the application of a chiral SPINOL-phosphoric acid in the asymmetric aminalization reaction [27]. Tian´s research group developed the synthesis of dihydroquinazolinones