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Catalytic asymmetric de novo construction of dihydroquinazolinone scaffolds via enantioselective decarboxylative [4+2] cycloadditions

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Abstract

The first de novo construction of enantioenriched dihydroquinazolinones via an intermolecular strategy has been established. This approach also represents the first catalytic asymmetric [4+2] cycloaddition of vinyl benzoxazinanones with sulfonyl isocyanates, which afforded chiral dihydroquinazolinones in high yields and excellent enantioselectivities (up to 98% yield, 99 : 1 er). This reaction not only confronts the great challenge in de novo construction of enantioenriched dihydroquinazolinone skeletons, but also advances the chemistry of decarboxylative cycloadditions involving vinyl benzoxazinanones.

Graphical abstract: Catalytic asymmetric de novo construction of dihydroquinazolinone scaffolds via enantioselective decarboxylative [4+2] cycloadditions

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Publication details

The article was received on 16 Oct 2018, accepted on 08 Nov 2018 and first published on 08 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC08282K
Citation: Chem. Commun., 2018, Advance Article
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    Catalytic asymmetric de novo construction of dihydroquinazolinone scaffolds via enantioselective decarboxylative [4+2] cycloadditions

    Y. Lu, J. Lan, Y. Mao, Y. Wang, G. Mei and F. Shi, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC08282K

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