Stereodivergent synthesis of C-glycosamino acids via Pd/Cu dual catalysis

Abstract

Herein, we reported the stereodivergent synthesis of C-glycosamino acids via Pd/Cu dual catalysis and found a suitable system to resolve many challenges, such as the tolerance towards the density of functional groups, the variability of the anomeric position, the compatibility of appropriate catalyst combinations, the regioselectivity of nucleophiles, and the match/mismatch problems between chiral substrates and chiral ligand-metal complexes. The method enables the efficient preparation of a series of unnatural C-glycosamino acid skeletons bearing two contiguous stereogenic centers in good yields with excellent diastereos-electivity. From this crucial precursor, various C-glycosamino acid derivatives have been achieved diversely. The readily prepared C-glycosamino acid hybrids will meet the growing demands for the development of new molecular entities for discovering new drugs and materials. This stereodivergent synthesis of C-glycosamino acids will further accelerate the study of their structural features, mode of action, and potential biological applications in the near future.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (051170001, 21772084, 22071087), the Fundamental Research Funds for the Central Universities (lzujbky-2017-k06) and the Open Projects Funds of Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University (2019CCG05). Xiaolei Wang thanks the Thousand Young Talents Program for financial support. We also thank Sumit O. Bajaj (Corden Pharma Boulder) for language polishing and Prof. Quanxiang Wu & Ya Li for giving suggestion towards the absolute configuration determining via CD spectra.

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Correspondence to Jian Liu or Xiaolei Wang.

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Yan, X., Feng, F., Zhou, L. et al. Stereodivergent synthesis of C-glycosamino acids via Pd/Cu dual catalysis. Sci. China Chem. (2021). https://doi.org/10.1007/s11426-020-9930-7

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Keywords

  • C-glycosamino acid
  • glycomimetics
  • peptidomimetics
  • stereodivergent
  • dual catalysis