title: TMSOTf mediated stereoselective synthesis of α-C-glycosides from unactivated aryl acetylenes.
abstract: A metal free and highly stereoselective procedure for the synthesis of 2,3-unsaturated-C-glycosides has been developed between glycals and unactivated aryl acetylenes in the presence of TMSOTf through a triflated C-vinyl glycosides intermediate. The flexibility of the procedure was tested by a wide variety of glycals and unactivated aryl acetylenes (20 examples). The corresponding alkynyl C-glycosides were obtained in good yields with completely α-selectivity in a short time (<25 min). And a plausible mechanism for the synthesis of alkynyl C-glycosides was depicted.
authors: School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, China.
authors: Heshan
authors: H
authors: Chen
authors: School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, China.
authors: Xiaosheng
authors: X
authors: Luo
authors: School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, China.
authors: Saifeng
authors: S
authors: Qiu
authors: School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, China.
authors: Wengjie
authors: W
authors: Sun
authors: School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, China. jbzhang@chem.ecnu.edu.cn.
authors: Jianbo
authors: J
authors: Zhang
mesh_terms: D000114:Acetylene / Q000031:analogs & derivatives / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D006027:Glycosides; D008698:Mesylates; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate; D000114:Acetylene
keywords: Aryl acetylenes; C-glycosides; Glycals; Metal free; TMSOTf