title: Iron(III) chloride as an efficient catalyst for stereoselective synthesis of glycosyl azides and a cocatalyst with Cu(0) for the subsequent click chemistry.
abstract: A highly efficient and mild method for azido glycosylation of glycosyl β-peracetates to 1,2-trans glycosyl azides was developed by using inexpensive FeCl(3) as the catalyst. In addition, we demonstrated, for the first time, that FeCl(3) in combination with copper powder can promote 1,3-dipolar cycloaddition (click chemistry) of azido glycosides with terminal alkynes. Good to excellent yields were obtained with exclusive formation of a single isomer in both glycosyl azidation and subsequent cycloaddition processes.
authors.affiliation: Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan.
authors.forename: Santosh B
authors.initials: SB
authors.lastname: Salunke
authors.forename: N Seshu
authors.initials: NS
authors.lastname: Babu
authors.forename: Chien-Tien
authors.initials: CT
authors.lastname: Chen
mesh_terms: D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry*; D006031:Glycosylation; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D001386:Azides; D002712:Chlorides; D005290:Ferric Compounds; D003300:Copper; C024555:ferric chloride