Issue 96, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
16 Oct 2018
Accepted
08 Nov 2018
First published
08 Nov 2018

Chem. Commun., 2018,54, 13527-13530

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, 54, 13527 DOI: 10.1039/C8CC08282K

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