Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis?

Organic & Biomolecular Chemistry Pub Date: 2013-02-11 DOI: 10.1039/C3OB40118A

Abstract

For too long the aromatic aza-Claisen rearrangement has been the poor relation of its oxygen counterpart. We demonstrate that on-water catalysis facilitates the rearrangement of reverse N-prenylated naphthylamines and anilines, and transforms the aromatic aza-Claisen rearrangement into a synthetically viable reaction. We use this reaction to probe the mechanism of on-water catalysis, and provide compelling support for the acid-catalysis hypothesis.

Graphical abstract: Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis
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