New Strategies for N-Heterocyclic Carbenes Catalyzed Annulations

New Strategies for N-Heterocyclic Carbenes Catalyzed Annulations

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English
123 Pages

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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.

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Published 20 December 2016
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EAN13 9789811028991
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Language English

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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.