Synthesis of Stannyl-Substituted D-Glucal Derivatives via Palladium-Catalyzed Regioselective Hydrostannation and Their Synthetic Applications

Autor(es)

Shamim, Anwar ; Barbeiro, Criatiane S. ; Ali, Bakhat ; Stefani, Helio A.

• Tipo de documento: Artigo Científico
• Fonte: CHEMISTRYSELECT; v. 1, n. 18, p. 5653-5659, NOV 1 2016.
• Citações Web of Science: 6

Resumo

Stannyl derivatives of 2-alkenyl acetylated D-glucals have been synthesized via palladium-catalyzed regioselective hydrostannation in good yields under mild reaction conditions. Factors affecting the regioselectivity of hydrostannation including chelation by the neighbouring acetyl-oxygen and the electronic effect of the substituent R on alkyne have been evaluated. The synthetic applications of these stannyl derivatives of D-glucal are shown by performing Stille and Sonogashira cross-coupling reactions to obtain a library of substituted 2-alkenyl derivatives of D-glucal. (AU)

• Processo FAPESP: 12/00424-2 - Síntese de pequenas bibliotecas empregando organotrifluoroboratos de potássio em reações de Suzuki-Miyaura
• Beneficiário: Helio Alexandre Stefani
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Processo FAPESP: 12/17954-4 - Reações de Ciclização de Acetil- e Etoxil-pirrolidin-2-onas com Sais de Organotrifluoroboratos de Potássio
• Beneficiário: Bakhat Ali
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado