TY - JOUR
T1 - Synthesis and Reactivity of Atropo-Diastereomeric Benzoazepine-Fused Isoindoles
AU - de Ceuninck van Capelle, Lillian A.
AU - Wales, Steven M.
AU - Macdonald, James M.
AU - Kruger, Megan
AU - Richardson, Christopher
AU - Gardiner, Michael G.
AU - Hyland, Christopher J.T.
N1 - Publisher Copyright:
© 2025 American Chemical Society.
PY - 2025/2/28
Y1 - 2025/2/28
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85218177732&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.4c03064
DO - 10.1021/acs.joc.4c03064
M3 - Article
AN - SCOPUS:85218177732
SN - 0022-3263
VL - 90
SP - 3101
EP - 3109
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 8
ER -