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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201712726
Subject(s) - thiourea , chemistry , glycosyl , halogen , catalysis , halogen bond , asparagine , combinatorial chemistry , organocatalysis , stereochemistry , organic chemistry , medicinal chemistry , enantioselective synthesis , alkyl , enzyme
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.