Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea
2020
Li, Qiuhan | Levi, Samuel M. | Jacobsen, Eric N.
We report highly β-selective bis-thioureas-catalyzed 1,2-cis-O-pyranosylations employing easily accessible acetonide-protected donors. A wide variety of alcohol nucleophiles, including complex natural products, glycosides, and amino acids were β-mannosylated and β-rhamnosylated successfully using an operationally simple protocol under mild and neutral conditions. Less nucleophilic acceptors such as phenols were also glycosylated efficiently in excellent yields and with high β-selectivities.
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