A novel base-induced isomerization gives access to unprecedented (E)-exo-glycals

Guillaume Eppe; Lidia Dumitrescu; Olivier Pierrot; Tianlei Li; Weidong Pan; Stéphane P. Vincent

doi:10.1002/chem.201300969

A novel base-induced isomerization gives access to unprecedented (E)-exo-glycals

Guillaume Eppe, Lidia Dumitrescu, Olivier Pierrot, Tianlei Li, Weidong Pan, Stéphane P. Vincent

Unit of organic chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Bump the base: This study reports the discovery of the base-induced Z-to-E isomerization of exo-glycals bearing an electron-withdrawing group (EWG). The scope of this novel transformation regarding the carbohydrate unit is also discussed. After elucidating the mechanism, preparation of novel (E)-exo- glycals was performed (TBS=tert-butyldimethylsilyl).

Original language	English
Pages (from-to)	11547-11552
Number of pages	6
Journal	Chemistry: A European Journal
Volume	19
Issue number	35
DOIs	https://doi.org/10.1002/chem.201300969
Publication status	Published - 26 Aug 2013

Keywords

carbohydrates
enol ethers
isomerization
phosphonates
stereochemistry

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10.1002/chem.201300969

Cite this

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abstract = "Bump the base: This study reports the discovery of the base-induced Z-to-E isomerization of exo-glycals bearing an electron-withdrawing group (EWG). The scope of this novel transformation regarding the carbohydrate unit is also discussed. After elucidating the mechanism, preparation of novel (E)-exo- glycals was performed (TBS=tert-butyldimethylsilyl).",

keywords = "carbohydrates, enol ethers, isomerization, phosphonates, stereochemistry",

author = "Guillaume Eppe and Lidia Dumitrescu and Olivier Pierrot and Tianlei Li and Weidong Pan and Vincent, {St{\'e}phane P.}",

year = "2013",

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doi = "10.1002/chem.201300969",

language = "English",

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AU - Eppe, Guillaume

AU - Dumitrescu, Lidia

AU - Pierrot, Olivier

AU - Li, Tianlei

AU - Pan, Weidong

AU - Vincent, Stéphane P.

PY - 2013/8/26

Y1 - 2013/8/26

N2 - Bump the base: This study reports the discovery of the base-induced Z-to-E isomerization of exo-glycals bearing an electron-withdrawing group (EWG). The scope of this novel transformation regarding the carbohydrate unit is also discussed. After elucidating the mechanism, preparation of novel (E)-exo- glycals was performed (TBS=tert-butyldimethylsilyl).

AB - Bump the base: This study reports the discovery of the base-induced Z-to-E isomerization of exo-glycals bearing an electron-withdrawing group (EWG). The scope of this novel transformation regarding the carbohydrate unit is also discussed. After elucidating the mechanism, preparation of novel (E)-exo- glycals was performed (TBS=tert-butyldimethylsilyl).

KW - carbohydrates

KW - enol ethers

KW - isomerization

KW - phosphonates

KW - stereochemistry

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DO - 10.1002/chem.201300969

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JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

IS - 35

ER -

A novel base-induced isomerization gives access to unprecedented (E)-exo-glycals

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Keywords

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Physical Chemistry and characterization(PC2)

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A novel base-induced isomerization gives access to unprecedented (E)-exo-glycals

Abstract

Keywords

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Physical Chemistry and characterization(PC2)

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