Direct N‐Glycofunctionalization of Amides with Glycosyl Trichloroacetimidate by Thiourea/Halogen Bond Donor Co‐Catalysis |
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| Authors: | Dr. Yusuke Kobayashi Yuya Nakatsuji Shanji Li Dr. Seiji Tsuzuki Prof. Dr. Yoshiji Takemoto |
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| Affiliation: | 1. Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto, Japan;2. Research Initiative of Computational Sciences (RICS), Nanosystem Research Institute (NRI), National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan |
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| Abstract: | Using a halogen bond (XB) donor and Schreiner's thiourea as cooperative catalysts, various amides, including the asparagine residues of several peptides, were directly coupled with glycosyl trichloroacetimidates to give unique N‐acylorthoamides in good yields. Synthetic applications of N‐acylorthoamides, including rearrangement to the corresponding β‐N‐glycoside, were also demonstrated. |
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| Keywords: | Brø nsted acid catalysis carbohydrates glycosylation organocatalysis |
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