Asymmetric Brønsted Acid Catalyzed Isoindoline Synthesis: Enhancement of Enantiomeric Ratio by Stereoablative Kinetic Resolution

Asymmetric Brønsted Acid Catalyzed Isoindoline Synthesis: Enhancement of Enantiomeric Ratio by Stereoablative Kinetic Resolution

Improving with time: The first catalytic asymmetric synthesis of chiral 1,3‐disubstituted isoindolines is based on a Brønsted acid catalyzed one‐pot reaction consisting of a Friedel–Crafts reaction and a base‐catalyzed aza‐Michael addition (see scheme). The enantiomeric ratio of the product signific...

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Veröffentlicht in:Angewandte Chemie International Edition 2008-01, Vol.47 (30), p.5661-5665
Hauptverfasser: Enders, Dieter, Narine, Arun A., Toulgoat, Fabien, Bisschops, Tom
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric catalysis
aza‐Michael addition
chiral Brønsted acids
Friedel–Crafts reaction
organocatalysis
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Zusammenfassung:Improving with time: The first catalytic asymmetric synthesis of chiral 1,3‐disubstituted isoindolines is based on a Brønsted acid catalyzed one‐pot reaction consisting of a Friedel–Crafts reaction and a base‐catalyzed aza‐Michael addition (see scheme). The enantiomeric ratio of the product significantly increases with reaction time as a result of a Brønsted acid catalyzed stereoablative kinetic resolution, which occurs in tandem to the first step.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200801354