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Direct N ‐Glycofunctionalization of Amides with Glycosyl Trichloroacetimidate by Thiourea/Halogen Bond Donor Co‐Catalysis
Author(s) -
Kobayashi Yusuke,
Nakatsuji Yuya,
Li Shanji,
Tsuzuki Seiji,
Takemoto Yoshiji
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201712726
Subject(s) - thiourea , chemistry , glycosyl , halogen , catalysis , medicinal chemistry , organic chemistry , combinatorial chemistry , alkyl
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.