Stereoselective preparation of trifluoromethyl containing 1,4-oxathiolane derivatives through ring expansion reaction of 1,3-oxathiolanes

Trifluoromethyl containing 1,4-oxathiolanes are synthesized in excellent yields and high stereoselectivities from the expansion reactions of sulfur ylide intermediates, which were prepared from the reaction of 2-diazo-3,3,3-trifluoro-propionic acid methyl ester and 1,3-oxathiolanes in the presence o...

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Bibliographic Details
Published in:Tetrahedron 2006-01, Vol.62 (5), p.829-832
Main Authors: Zhu, Shifa, Xing, Chunhui, Zhu, Shizheng
Format: Article
Language:English
Subjects:
1,4-Oxathiolane
Diastereomeric ratio
Diazo
Lipophilicity
Stereoselective synthesis
Sulfur ylide
Trifluoromethyl
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Summary:Trifluoromethyl containing 1,4-oxathiolanes are synthesized in excellent yields and high stereoselectivities from the expansion reactions of sulfur ylide intermediates, which were prepared from the reaction of 2-diazo-3,3,3-trifluoro-propionic acid methyl ester and 1,3-oxathiolanes in the presence of Rh 2(OAc) 4. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.10.050