Revisiting the Reaction of Sulfur Ylides with Acetylenic Esters: Synthesis of Trisubstituted 1,3-Dienes, α-Carbonyl Vinyl Sulfoxides and α-Carbonyl Vinyl Sulfoxonium Ylides

Autor(es)

de Jesus, Matheus P. ; Burtoloso, Antonio C. B.

• Tipo de documento: Artigo Científico
• Fonte: CHEMISTRY-AN ASIAN JOURNAL; v. 19, n. 23, p. 7-pg., 2024-10-28.

Resumo

We report herein a reexamination of the reactions between sulfoxonium ylides and acetylenic esters. Continuing our previous study of conjugate additions using alpha-carbonyl sulfoxonium ylides, we came across an interesting transformation when dimethyl acetylenedicarboxylate (DMAD) was employed as a Michael acceptor. Trisubstituted electron-deficient 1,3-dienes and alpha-carbonyl vinyl sulfoxides were obtained for the first time from these sulfur ylides, in a stereoselective manner (exclusively forming the E-isomer), achieving yields of up to 70 % and 83 %, respectively. Selected dienes were subsequently utilized in the synthesis of novel nitrogen heterocycles. Interestingly, when di-tert-butyl acetylenedicarboxylate (DtBAD) or alkyl propiolates were evaluated, the isolated product arose from the classical Michael addition, yielding alpha-carbonyl vinyl sulfoxonium ylides in yields of up to 89 %. (AU)

• Processo FAPESP: 20/07143-5 - Estudos visando à preparação de ilídeos ²-ceto sulfoxônios -ceto sulfoxônios pró-quirais alquilados e suas aplicações na síntese de derivados de isoquinolina
• Beneficiário: Matheus Pereira de Jesus
• Modalidade de apoio: Bolsas no Brasil - Doutorado Direto
• Processo FAPESP: 20/15230-5 - Centro de Pesquisa e Inovação de Gases de Efeito Estufa - RCG2I
• Beneficiário: Julio Romano Meneghini
• Modalidade de apoio: Auxílio à Pesquisa - Programa Centros de Pesquisa em Engenharia
• Processo FAPESP: 23/02675-7 - Novas metodologias para formação de ligações C-C a partir de ilídeos sulfoxônios
• Beneficiário: Antonio Carlos Bender Burtoloso
• Modalidade de apoio: Auxílio à Pesquisa - Regular