Issue 38, 2016

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

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

Supplementary files

Article information

Article type
Paper
Submitted
01 Mar 2016
Accepted
22 Mar 2016
First published
24 Mar 2016
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2016,6, 31861-31870

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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