Catalytic asymmetric de novo construction of dihydroquinazolinone scaffolds via enantioselective decarboxylative
Yi-Nan Lu1, Jin-Ping Lan1, Yu-Jia Mao1
1School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116, China. fshi@jsnu.edu.cn guangjianM@jsnu.edu.cn.
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.
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives
Criteria for Aromaticity and the Hückel 4n + 2 Rule
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n +...
Cycloaddition Reactions: Overview


