Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study

The first asymmetric synthesis of 3-amino-substituted isoindolinones was accomplished via cascade hemiaminal-heterocyclization-intramolecular aza-Mannich reaction of benzylamines and 2-formylbenzonitriles using chiral phase transfer conditions (PTC). A theoretical study of the enantioselective step...

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Bibliographic Details
Published in:RSC advances 2016, Vol.6 (38), p.31861-31870
Main Authors: Capobianco, Amedeo, Di Mola, Antonia, Intintoli, Valentina, Massa, Antonio, Capaccio, Vito, Roiser, Lukas, Waser, Mario, Palombi, Laura
Format: Article
Language:English
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Summary:The first asymmetric synthesis of 3-amino-substituted isoindolinones was accomplished via cascade hemiaminal-heterocyclization-intramolecular aza-Mannich reaction of benzylamines and 2-formylbenzonitriles using chiral phase transfer conditions (PTC). A theoretical study of the enantioselective step provides a rationale for the mode of action of the best performing phase transfer catalyst and the observed face selectivity.
ISSN:2046-2069
2046-2069
DOI:10.1039/C6RA05488A