Cyclisation of Propargyl and Allyl Amides: Syntheses of Oxazolines

This thesis describes several approaches to the synthesis of dihydrooxazoles (oxazolines) by the cyclisation of unsaturated amides. The first major approach to the synthesis of substituted dihydrooxazoles is the CuI-catalysed cycloisomerisation of terminal propargyl amides. The reaction has been shown to have good substrate scope and experiments to delineate the mechanism have been performed. Substrates containing a benzylic methylene were oxidised to the ketone under the reaction conditions. The second major focus of this thesis is the cyclisation of N-alkenylamides catalysed by iodoarenes under oxidative conditions. Dihydrooxazoles were prepared by this route with a range of substitution patterns in good yields

Iodoarene-Catalyzed Cyclizations of Unsaturated Amides

The cyclization of N-alkenylamides catalyzed by iodoarenes under oxidative conditions is presented. Five-, six-, and seven-membered rings with a range of substitutions can be prepared by this route. Preliminary data from the use of chiral iodoarenes as precatalysts show that enantiocontrol is feasible

CuI-catalyzed cycloisomerization of propargyl amides

The synthesis of substituted dihydrooxazoles by the CuI-catalyzed cycloisomerization of terminal propargyl amides is reported. The reaction has been shown to have good substrate scope and experiments to delineate the mechanism have been performed. Substrates containing a benzylic methylene were oxidized to the ketone under the reaction conditions