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

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

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.

langue originale	Anglais
Pages (de - à)	6769-6773
Nombre de pages	5
journal	Organic Letters
Volume	20
Numéro de publication	21
Les DOIs	https://doi.org/10.1021/acs.orglett.8b02891
Etat de la publication	Publié - 2 nov. 2018

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10.1021/acs.orglett.8b02891

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

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.",

author = "Fr{\'e}d{\'e}ric, {Christophe J.M.} and J{\'e}r{\^o}me Cornil and Mathilde Vandamme and Lidia Dumitrescu and Abdellatif Tikad and Rapha{\"e}l Robiette and Vincent, {St{\'e}phane P.}",

year = "2018",

month = nov,

day = "2",

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

language = "English",

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pages = "6769--6773",

journal = "Organic Letters",

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T1 - Highly (Z)-Diastereoselective Synthesis of Trifluoromethylated exo-Glycals via Photoredox and Copper Catalysis

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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U2 - 10.1021/acs.orglett.8b02891

DO - 10.1021/acs.orglett.8b02891

M3 - Article

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AN - SCOPUS:85055004568

SN - 1523-7060

VL - 20

SP - 6769

EP - 6773

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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