New Strategies for N-Heterocyclic Carbenes Catalyzed Annulations

This thesis focuses on NHC-catalyzed annulation of nitroalkenes, enals and a,ß-unsaturated carboxylic acids. (1) NHCs were found to be efficient catalysts for the [4+2] annulation of ß-substituted nitroalkenes. The scope of Rauhut-Currier reaction was successfully extended to the most challenging ß-substituted alkenes by this method; (2) Enals were successfully used for [4+2] annulations with azodicarboxylates catalyzed by NHC via -addition. Highly enantiopure tetrahydropyridazinones and -amino acid derivatives could be easily prepared by subsequent transformations of the resulting dihydropyridazinones. (4) The readily available a,ß-unsaturated carboxylic acids were first successfully employed to generate the a,ß-unsaturated acyl azolium intermediates by using NHC for the enantioselective [3+2] and [3+3] annulations.

Klappentext

This thesis focuses on NHC-catalyzed annulation of nitroalkenes, enals and ,-unsaturated carboxylic acids. (1) NHCs were found to be efficient catalysts for the [4+2] annulation of -substituted nitroalkenes. The scope of RauhutCurrier reaction was successfully extended to the most challenging -substituted alkenes by this method; (2) Enals were successfully used for [4+2] annulations with azodicarboxylates catalyzed by NHC via -addition. Highly enantiopure tetrahydropyridazinones and -amino acid derivatives could be easily prepared by subsequent transformations of the resulting dihydropyridazinones. (4) The readily available ,-unsaturated carboxylic acids were first successfully employed to generate the ,-unsaturated acyl azolium intermediates by using NHC for the enantioselective [3+2] and [3+3] annulations.

Inhalt

Introduction.- NHC-catalyzed Annulations of Nitroalkenes.- NHC-catalyzed Enantioselective Annulations of Enals.- NHC-catalyzed Enantioselective Annulations of ,-unsaturated Carboxylic Acids.- Experimental Part.- Research Summary.