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

Christophe J.M. Frédéric, Jérôme Cornil, Mathilde Vandamme, Lidia Dumitrescu, Abdellatif Tikad, Raphaël Robiette, Stéphane P. Vincent

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)6769-6773
Number of pages5
JournalOrganic Letters
Volume20
Issue number21
DOIs
Publication statusPublished - 2 Nov 2018

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