2021Beilstein Journal of Organic ChemistryOpen access

Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes

Martin Kamlar, Róbert Reiberger, Martin Nigríni, Ivana Cı́sařová, Ján Veselý

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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%).

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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%).

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Available 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%).

Key concepts: Enantioselective synthesis, Stereocenter, Chemistry, Brønsted–Lowry acid–base theory, Catalysis, Combinatorial chemistry, Organocatalysis, Carbon fibers

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