Photoinduced Regio- and Stereoselective Hydrotrifluoromethylation of Glycals with Langlois Reagent
Tian Li1, Miao Liu1, Zhao-Xiang Luo1
1State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.
Abstract:
Fluorination has demonstrated the potential to improve the physicochemical and enzymatic properties of carbohydrates. Hydrotrifluoromethylation is an emerging reaction to introduce trifluoromethyl groups. However, the hydrotrifluoromethylation of glycals has been challenging because of the lack of regioselectivity and stereoselectivity. Herein, we describe an efficient, highly selective, and broadly applicable photoinduced hydrotrifluoromethylation strategy of glycals using cost-effective sodium trifluoromethanesulfonate to give 1,2-dideoxy-2-trifluoromethyl sugars.
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