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Issue 38, 2016
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Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study

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Abstract

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.

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

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Article information


Submitted
01 Mar 2016
Accepted
22 Mar 2016
First published
24 Mar 2016

This article is Open Access

RSC Adv., 2016,6, 31861-31870
Article type
Paper

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

A. Capobianco, A. Di Mola, V. Intintoli, A. Massa, V. Capaccio, L. Roiser, M. Waser and L. Palombi, RSC Adv., 2016, 6, 31861
DOI: 10.1039/C6RA05488A

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