Highly (Z)-Diastereoselective Synthesis of Trifluoromethylated exo-Glycals via Photoredox and Copper Catalysis

Frédéric, Christophe J.-M.;Cornil, Jérôme;Vandamme, Mathilde;Dumitrescu, Lidia;Vincent, Stéphane P.;et.al.
(2018) Organic Letters — Vol. 20, n° 21, p. 6769-6773 (2018)

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Authors
  • Frédéric, Christophe J.-M.
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  • Cornil, Jérôme
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  • Vandamme, Mathilde
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  • Dumitrescu, Lidia
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  • Vincent, Stéphane P.orcid-logo
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Abstract
Highly (Z)-diastereoselective approaches for the synthesis of trifluoromethylated exo-glycals by copper and photoredox catalysis are described. These complementary reactions are applicable to a wide range of methylene exo-glycals generated from the corresponding pyranoses and furanoses and give trifluoromethylated compounds under mild conditions in moderate to good yields. DFT calculations have allowed a rationalization of the observed (Z)-stereoselectivity.
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Citations

Frédéric, C. J.-M., Cornil, J., Vandamme, M., Dumitrescu, L., Tikad, A., Robiette, R., & Vincent, S. P. (2018). Highly (Z)-Diastereoselective Synthesis of Trifluoromethylated exo-Glycals via Photoredox and Copper Catalysis. Organic Letters, 20(21), 6769-6773. https://doi.org/10.1021/acs.orglett.8b02891 (Original work published 2018)