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