Intermolecular Stetter Reactions on Morita-Baylis-Hillman Adducts: an Approach to Highly Functionalized 1,4-Dicarbonyl Compounds

Autor(es)

Gomes, Ralph C. ; Barcelos, Rosimeire C. ; Rodrigues, Jr., Manoel T. ; Santos, Hugo ; Coelho, Fernando

• Tipo de documento: Artigo Científico
• Fonte: CHEMISTRYSELECT; v. 2, n. 3, p. 926-930, JAN 2017.
• Citações Web of Science: 0

Resumo

We reported herein an N-heterocyclic carbene (NHC)-mediated intermolecular Stetter reaction between oxidized Morita-Baylis-Hillman (MBH) adducts and a variety of aldehydes. This protocol allows the synthesis of highly functionalized 1,4-dicarbonyl compounds. The reaction is an alternative approach to these compounds using commercially available starting materials. This metal-free process exhibits a wide substrate scope, excellent atom economy, compatibility with functionalized substrates and mild reaction conditions. The 1,4-dicarbonyl compounds were prepared in two steps via MBH reactions with overall yields up to 99%. This protocol is easily scalable. The synthetic usefulness of this method was demonstrated in a high yield synthesis of a tri-substituted pyrrole used as an advanced intermediate in the total synthesis of kinase inhibitors as well as in the synthesis of another heterocycles. (AU)

• Processo FAPESP: 13/10449-5 - Adutos de Morita-Baylis-Hillman como blocos de contrução eficientes para a síntese de moléculas de interesse biológico
• Beneficiário: Fernando Antonio Santos Coelho
• Linha de fomento: Auxílio à Pesquisa - Regular
• Processo FAPESP: 13/07600-3 - CIBFar - Centro de Inovação em Biodiversidade e Fármacos
• Beneficiário: Glaucius Oliva
• Linha de fomento: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs
• Processo FAPESP: 15/09205-0 - Novas fronteiras da reação de Morita-Baylis-Hillman: 1) Novas aplicações de um catalisador bifuncional derivado do imidazol. 2) Estudos visando à síntese assimétrica de um adoçante natural com alto potencial dulcífero
• Beneficiário: Hugo dos Santos
• Linha de fomento: Bolsas no Brasil - Doutorado Direto