Organocatálise assimétrica e sistemas vinílogos: adição de 1,3-oxazolina-2-tionas a aldeídos a,b-insaturados

• Ano de defesa: 2017
• Autor(a) principal: Matsuo, Bianca Taeko
• Orientador(a): Paixão, Márcio Weber
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal de São Carlos; Câmpus São Carlos
• Programa de Pós-Graduação: Programa de Pós-Graduação em Química - PPGQ
• Palavras-chave em Português: Organocatálise; 1,3-oxazolina-2-tionas; Adição de Michael; Síntese assimétrica
• Área do conhecimento CNPq: CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::SINTESE ORGANICA; CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
• Link de acesso: https://repositorio.ufscar.br/handle/20.500.14289/13734

The use of organic molecules in stereoselective transformations has emerged as a powerful tool for the efficient construction of chiral skeletons and complementing existing methods. Currently, a great variety of reactions using organocatalytic methods (Diels-Alder and cycloadditions in general, Mannich and Michael aldol reactions, epoxidation, α-halogenation, amination, among others) has been developed for the formation of new C-C bonds, being important for the continuous advances of this field of asymmetric catalysis the application of new methodologies, catalysts and substrates. In this work, we explored the reactivity of 1,3-oxazoline-2-thiones scaffolds as Michael donors in organocatalyzed conjugated reactions to a,b-unsaturated aldehydes. By using the Jørgensen organocatalyst it was possible to obtain the functionalized heterocyclic compounds in high yield with ee up to 99% and 9:1 d.r.