Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes

Martin Kamlar; Robert Reiberger; Martin Nigríni; Ivana Císařová; Jan Veselý

doi:10.3762/bjoc.17.160

Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes

Beilstein J Org Chem. 2021 Sep 16:17:2433-2440. doi: 10.3762/bjoc.17.160. eCollection 2021.

Authors

Martin Kamlar¹, Robert Reiberger¹, Martin Nigríni¹, Ivana Císařová², Jan Veselý¹

Affiliations

¹ Department of Organic Chemistry Charles Univerzity, Hlavova 2030/8, Prague 2, 12800, Czech Republic.
² Department of Inorganic Chemistry, Charles Univerzity, Hlavova 2030/8, Prague 2, 12800, Czech Republic.

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: Brønsted acid; PCCP; aminalization; organocatalysis; pentacarboxycyclopentadiene.

Grants and funding

The work was supported by the Czech Science Foundation (20-29336S). This work has been supported by Charles University Research Centre program No. UNCE/SCI/014. The authors acknowledge the support of the Charles University program START No. CZ.02.2.69/0.0/0.0/19_073/0016935 (START/SCI/084).