Previous glycosylation strategies typically rely on Lewis acidic or oxidative activation of glycosyl donors to achieve high reactivity, resulting in poor functional group compatibility. The regio- and stereoselectivity of a given coupling reaction are controlled by employing complex protecting group combinations. However, a general solution that is compatible with sensitive functional groups and enables efficient catalyst-controlled regio- and stereoselective glycosylation across a broad range of substrates is still currently lacking. Toward this goal, we have developed a strategy relying on bis-thiourea catalysts to control the regio- and stereoselectivity of coupling reactions, generating both <i>cis</i>-1,2-β- and <i>trans</i>-1,2-β-linkages with acceptors possessing sensitive functional groups under mild conditions. When unprotected glycosyl acceptors were employed, high catalyst-controlled site-selectivity was also achieved with excellent anomeric selectivity.

Catalyst-controlled regio- and stereoselective glycosylation

2019 Fall National Meeting

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