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Asymmetric Brønsted Acid Catalyzed Isoindoline Synthesis: Enhancement of Enantiomeric Ratio by Stereoablative Kinetic Resolution
Author(s) -
Enders Dieter,
Narine Arun A.,
Toulgoat Fabien,
Bisschops Tom
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200801354
Subject(s) - isoindoline , kinetic resolution , enantiomer , catalysis , chemistry , resolution (logic) , kinetic energy , enantioselective synthesis , stereochemistry , medicinal chemistry , organic chemistry , computer science , physics , artificial intelligence , quantum mechanics
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.