Study of the Stereoselectivity of the Nucleophilic Epoxidation of 3-Hydroxy-2- methylene Esters

The diastereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters has been studied. The 3-hydroxy-2-methylene esters were obtained through a Morita–Baylis–Hillman reaction. The resulting epoxyesters were treated with thiophenol for transformation into 2,3-dihydroxy-2-((phenylt...

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Bibliographic Details
Published in:Tetrahedron
Main Authors: Latorre, Antonio, Sáez Cases, José Antonio, Rodríguez, Santiago, González, Florenci
Format: Article in Journal/Newspaper
Language:English
Published: Elsevier 2014
Subjects:
chemical reaction
epoxidation
Morita Baylis Hillman reaction
nucleophilicity
stereochemistry
carbonic acid derivative
ester derivative
thiophenol derivative
Carbonic acid
Online Access:http://hdl.handle.net/10234/88869
https://doi.org/10.1016/j.tet.2013.11.014
Description
Summary:The diastereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters has been studied. The 3-hydroxy-2-methylene esters were obtained through a Morita–Baylis–Hillman reaction. The resulting epoxyesters were treated with thiophenol for transformation into 2,3-dihydroxy-2-((phenylthio)methyl), which upon treatment with triphosgene afforded the corresponding cyclic carbonates.

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