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

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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.

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Acknowledgments

This project was financially supported by Natural Science Foundation of Shanghai (11ZR1410400), “DAXIA” Foundation of East China Normal University (No. 2011DX-288) National Students Innovative Experimental Projects (No. 1310269021) and large instruments Open Foundation of East China Normal University (2014-03&20151043).

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Authors and Affiliations

  1. School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, China

    Heshan Chen, Xiaosheng Luo, Saifeng Qiu, Wengjie Sun & Jianbo Zhang

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  1. Heshan Chen
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  2. Xiaosheng Luo
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  3. Saifeng Qiu
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  4. Wengjie Sun
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  5. Jianbo Zhang
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Correspondence to Jianbo Zhang.

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Chen, H., Luo, X., Qiu, S. et al. TMSOTf mediated stereoselective synthesis of α-C-glycosides from unactivated aryl acetylenes. Glycoconj J 34, 13–20 (2017). https://doi.org/10.1007/s10719-016-9718-7

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  • DOI: https://doi.org/10.1007/s10719-016-9718-7

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