Synthesis of Amine-Containing Heterocycles by Metathesis Reactions: Recent Advances and Opportunities

Abstract

Metathesis is one of the most powerful methods to access amine-containing heterocycles. However, the ability of amine to coordinate to the metal centre of almost all metathesis catalysts may limit the efficiency of this strategy. To date, the main approach to overcome these unwanted coordination events has been based on deactivation of the nitrogen atom by an electron-withdrawing protecting group. Basic amines are nevertheless not incompatible with metathesis reactions as shown by numerous recent examples described in the literature. The purpose of this review is to provide an overview of successful metathesis reactions performed with amine-containing substrates to access azacycles. The focus will be made on the different parameters that may favor the metathesis process including steric effects, amine basicity, and the nature of the catalyst.