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

Author(s)

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

• Document type: Journal article
• Source: CHEMISTRYSELECT; v. 1, n. 18, p. 5653-5659, NOV 1 2016.
• Web of Science Citations: 6

Abstract

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)

• FAPESP's process: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions
• Grantee: Helio Alexandre Stefani
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 12/17954-4 - Cyclization reaction of Acetyl- and Ethylpyrrolidin-2-one with Potassium Organotrifluoroborate Salts
• Grantee: Bakhat Ali
• Support Opportunities: Scholarships in Brazil - Post-Doctoral