Issue 21, 2014

A general overview of the organocatalytic intramolecular aza-Michael reaction

Abstract

The organocatalytic intramolecular aza-Michael reaction gives access to enantiomerically enriched nitrogen-containing heterocycles in a very simple manner. Enals, enones, conjugated esters and nitro olefins have been employed as Michael acceptors, while moderate nitrogen nucleophiles such as sulphonamides, carbamates and amides have been shown to be appropriate Michael donors in this type of reaction. Additionally, the process has been performed under both covalent and non-covalent catalysis, with diaryl prolinols, imidazolidinones, thioureas and chiral binol phosphoric acids being the most frequently used catalysts. The level of efficiency reached with this protocol is demonstrated by the implementation of numerous tandem processes, as well as the total synthesis of several natural products.

Graphical abstract: A general overview of the organocatalytic intramolecular aza-Michael reaction

Article information

Article type
Review Article
Submitted
07 May 2014
First published
18 Aug 2014

Chem. Soc. Rev., 2014,43, 7430-7453

Author version available

A general overview of the organocatalytic intramolecular aza-Michael reaction

M. Sánchez-Roselló, J. L. Aceña, A. Simón-Fuentes and C. del Pozo, Chem. Soc. Rev., 2014, 43, 7430 DOI: 10.1039/C4CS00156G

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