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

doi:10.1021/acs.orglett.8b02891

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 journal › Article › peer-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 language	English
Pages (from-to)	6769-6773
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.8b02891
Publication status	Published - 2 Nov 2018

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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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doi = "10.1021/acs.orglett.8b02891",

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AU - Frédéric, Christophe J.M.

AU - Cornil, Jérôme

AU - Vandamme, Mathilde

AU - Dumitrescu, Lidia

AU - Tikad, Abdellatif

AU - Robiette, Raphaël

AU - Vincent, Stéphane P.

PY - 2018/11/2

Y1 - 2018/11/2

N2 - 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.

AB - 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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JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

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

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