Synthesis and Reactivity of Atropo-Diastereomeric Benzoazepine-Fused Isoindoles
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de Ceuninck van Capelle, Lillian A.
Wales, Steven M.
Macdonald, James M.
Kruger, Megan
Richardson, Christopher
Gardiner, Michael G.
Hyland, Christopher J.T.
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Abstract
The stereoselective oxidation of benzoazepine-fused isoindolines to benzoazepine-fused isoindole atropodiastereomers is investigated, revealing a central-to-axial chirality conversion. By leveraging the characteristic folded conformation of these C-N atropisomers, Diels-Alder cycloaddition of the isoindole is achieved with complete facial selectivity, generating sp3-rich structures as single isomers.
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Journal of Organic Chemistry
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