TMSOTf mediated stereoselective synthesis of α-C-glycosides from unactivated aryl acetylenes

@article{Chen2016TMSOTfMS,
  title={TMSOTf mediated stereoselective synthesis of $\alpha$-C-glycosides from unactivated aryl acetylenes},
  author={Heshan Chen and Xiaosheng Luo and Saifeng Qiu and Weng-Jie Sun and Jianbo Zhang},
  journal={Glycoconjugate Journal},
  year={2016},
  volume={34},
  pages={13-20}
}
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… Expand
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