Control of site selectivity is a key challenge in synthetic carbohydrate chemistry. Building on the well-established interactions of boron compounds with diol groups in sugars, my group has explored the development of catalysts and reagents for selective functionalizations of OH groups in carbohydrate derivatives. We have identified diarylborinic acids (Ar<sub>2</sub>BOH) as useful catalysts for activation of diol moieties towards monofunctionalization reactions. Selective derivatizations of sugars that exploit this activation mode, along with mechanistic studies of the organoboron-catalyzed processes, will be discussed. Arylboronic acids display distinct reactivity with sugars, enabling transient protection of diol groups through the formation of boronic esters. This type of transient protection can also be harnessed to achieve otherwise challenging transformations of carbohydrates.

Organoboron catalysts and reagents for site-selective transformations of carbohydrate derivatives

2019 Spring National Meeting

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