As we slowly deplete our reserves of petroleum-based fuels while damaging the global landscape through their extraction, biomass is an attractive sustainable alternative towards the future of energy and materials. Sugar molecules from natural sources are rich in oxygen and chiral information. The development of chemoselective organic transformations around carbohydrates is challenging due to the variety of C-O bonds. Boron and silylium-based methods for the selective reduction and cyclization of carbohydrates are useful tools to increase the chemical space of chiral alcohols. In this presentation, we outline the expansion of this methodology toward the chemoselective functionalization of cheap and renewable sugar molecules with silyl nucleophiles under mild reaction conditions through boron and silyium ion catalysis.

Boron and silylium ion catalyzed functionalization of carbohydrates

ACS Spring 2022

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