Ferrier Reaction: The first synthesis of 2,3-unsaturated seleno-glycosides by using alkyl(aryl) hydroselenides as the nucleophile and Hf(OTf)4 as the catalyst |
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| Authors: | Peiran Chen Yajun Ding Saisai Guo Xiaoying Zhang |
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| Affiliation: | 1. Key Lab of Eco-Textile, The Ministry of Education, Donghua University, 2999 Renmin Road North, Songjiang District, Shanghai 201620, China;2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032, China |
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| Abstract: | ![]()
By using Hf(OTf)4 as the catalyst, a series of 2,3-unsaturated-Se-glucosides have been synthesized for the first time from tri-O-acetyl-d-glucal, 2,4,6-tri-O-benzyl-d-glucal, 3,4-di-O-acetyl-l-rhamnal and ((2R,3S)-3-acetoxy-2,3-dihydrofuran-2-yl) methyl acetate with PhSeH or alkyl(aryl) hydroselenides as the nucleophile in good yield and high anomeric selectivity. |
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| Keywords: | PhSeH Ferrier Reaction |
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