Issue 1, 2013

Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis

Abstract

The merged inverse-electron-demand hetero-Diels–Alder (ihDA)/retro-Diels–Alder (rDA) reaction sequence can be used to rapidly synthesise highly functionalised nitrogen heteroaromatics. The reaction offers many advantages: high atom economy, high levels of regioselectivity, it rarely requires a catalyst and, in some cases, can be performed in the absence of solvent. In this tutorial review we discuss the range of commonly used dienophiles and aza-dienes for this process whilst highlighting the reactivity trends, and illustrating their applications.

Graphical abstract: Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis

Article information

Article type
Tutorial Review
Submitted
06 Aug 2012
First published
19 Oct 2012

Chem. Soc. Rev., 2013,42, 63-76

Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis

R. A. A. Foster and M. C. Willis, Chem. Soc. Rev., 2013, 42, 63 DOI: 10.1039/C2CS35316D

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