Synthesis and Reactivity of Atropo-Diastereomeric Benzoazepine-Fused Isoindoles

Lillian A. de Ceuninck van Capelle; Steven M. Wales; James M. Macdonald; Megan Kruger; Christopher Richardson; Michael G. Gardiner; Christopher J.T. Hyland

doi:10.1021/acs.joc.4c03064

Synthesis and Reactivity of Atropo-Diastereomeric Benzoazepine-Fused Isoindoles

Lillian A. de Ceuninck van Capelle, Steven M. Wales, James M. Macdonald, Megan Kruger, Christopher Richardson, Michael G. Gardiner, Christopher J.T. Hyland^*

^*Corresponding author for this work

Research School of Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	3101-3109
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	90
Issue number	8
DOIs	https://doi.org/10.1021/acs.joc.4c03064
Publication status	Published - 28 Feb 2025

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10.1021/acs.joc.4c03064

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title = "Synthesis and Reactivity of Atropo-Diastereomeric Benzoazepine-Fused Isoindoles",

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.",

author = "\{de Ceuninck van Capelle\}, \{Lillian A.\} and Wales, \{Steven M.\} and Macdonald, \{James M.\} and Megan Kruger and Christopher Richardson and Gardiner, \{Michael G.\} and Hyland, \{Christopher J.T.\}",

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doi = "10.1021/acs.joc.4c03064",

language = "English",

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journal = "Journal of Organic Chemistry",

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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.

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 - https://www.scopus.com/pages/publications/85218177732

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 -

Synthesis and Reactivity of Atropo-Diastereomeric Benzoazepine-Fused Isoindoles

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