Catalytic activation of glycosyl phosphates for stereoselective coupling reactions.

Levi, Samuel M; Li, Qiuhan; Rötheli, Andreas R; Jacobsen, Eric N · Proc Natl Acad Sci U S A · 2019

basic_science · Level V

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Abstract

Glycosyl phosphates are shown to be activated to stereospecific nucleophilic substitution reactions by precisely tailored bis-thiourea catalysts. Enhanced reactivity and scope is observed with phosphate relative to chloride leaving groups. Stronger binding (K<sub>m</sub>) to the H-bond donor and enhanced reactivity of the complex (k<sub>cat</sub>) enables efficient catalysis with broad functional group compatibility under mild, neutral conditions.

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