Direct N‐Glycofunctionalization of Amides with Glycosyl Trichloroacetimidate by Thiourea/Halogen Bond Donor Co‐Catalysis. Issue 14 (5th March 2018)

• Record Type: Journal Article
• Authors: Kobayashi, Yusuke; Nakatsuji, Yuya; Li, Shanji; Tsuzuki, Seiji; Takemoto, Yoshiji
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 14(2018)
• Page Start: 3646
• Page End: 3650
• Publication Date: 2018-03-05
• Subjects: Brønsted acid catalysis -- carbohydrates -- glycosylation -- organocatalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201712726
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : Transformation of amides : Using a halogen bond (XB) donor and Schreiner's thiourea as cooperative catalysts, various amides 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 ‐glycosides, were also demonstrated.