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Aplicação de Aminoguanidinas em organocatálise
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Catálise é uma área de bastante importância em química orgânica, e o estudo desta disciplina é essencial para o desenvolvimento de uma química mais sustentável e limpa.
Este trabalho teve como principal objetivo o estudo de aminoguanidinas cíclicas como catalisadores em reações de Adição de Michael, a sua atividade e sua estereoespecificidade. Estas pequenas moléculas orgânicas foram acopladas a nanopartículas metálicas magnéticas (MNPs), suporte que foi testado a sua reprodutibilidade e sua vantagem magnética em Work-ups.
Primeiro sintetizou-se o catalisador que contou com 4 passos principais:
começando com a funcionalização das MNPs com uma amina primária, neste caso APTES. Depois seguiu-se a adição de uma prolina protegida. O terceiro passo foi a desproteção para, por fim, ligar uma carbodiimida, obtendo uma aminoguanidina cíclica.
Para o estudo do catalisador usou-se uma reação de adição de Michael onde o produto obtido possui dois centros assimétricos, e através de 1HNMR e de HPLC em faze estacionária quiral foi possível verificar o excesso enantiomérico e diastereomérico, podendo tirar conclusões em relação à atividade do catalisador desenvolvido
Catalysis is an area of great importance in organic chemistry, and the studyof this field is essential for the development of a more sustainable and clean chemical process. This work had as its focus the study of cyclical aminoguanidines as catalysts for the Michael Addition Reaction, its activity and its stereospecificity. Thesesmall organic molecules were coupled with metallic Magnetic Nanoparticles (MNPs), this support was tested for its reproducibility and its magnetic advantage in Work-ups. First, the catalyst was synthesized in 4 main steps: starting with the functionalisation of the MNPs with a primary amine, in this case APTES. Afterwards, a protected proline was added. The third step was the deprotection and, lastly, connection with a carbodiimide, obtaining a cyclical aminoguanidine. Michael’s Addition Reaction was used to study the catalyst, where the obtained product has two asymmetrical centres and, through 1HNMR and HPLC in chiral stationary phase it was possible to determine the enantiomeric and diastereomeric excess, conclusions about the developed catalyst’s activity were determined.
Catalysis is an area of great importance in organic chemistry, and the studyof this field is essential for the development of a more sustainable and clean chemical process. This work had as its focus the study of cyclical aminoguanidines as catalysts for the Michael Addition Reaction, its activity and its stereospecificity. Thesesmall organic molecules were coupled with metallic Magnetic Nanoparticles (MNPs), this support was tested for its reproducibility and its magnetic advantage in Work-ups. First, the catalyst was synthesized in 4 main steps: starting with the functionalisation of the MNPs with a primary amine, in this case APTES. Afterwards, a protected proline was added. The third step was the deprotection and, lastly, connection with a carbodiimide, obtaining a cyclical aminoguanidine. Michael’s Addition Reaction was used to study the catalyst, where the obtained product has two asymmetrical centres and, through 1HNMR and HPLC in chiral stationary phase it was possible to determine the enantiomeric and diastereomeric excess, conclusions about the developed catalyst’s activity were determined.