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

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 dihydroquinazolinon...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018-12, Vol.54 (96), p.13527-13530
Main Authors: Lu, Yi-Nan, Lan, Jin-Ping, Mao, Yu-Jia, Wang, Ye-Xin, Mei, Guang-Jian, Shi, Feng
Format: Article
Language:English
Subjects:
Catalysis
Crystallography
Cycloaddition
Enantiomers
Isocyanates
NMR
Nuclear magnetic resonance
Organic chemistry
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc08282k