A general stereoselective method for the synthesis of cyclopropanecarboxylates. A new version of the homologous Horner-Wadsworth-Emmons reaction.
The synthesis of alpha-, beta- and gamma-substituted alpha-phosphono-gamma-lactones was accomplished using different ring closure and ring homologation strategies. It was found that the lactones could be selectively transformed into the corresponding ethyl cyclopropanecarboxylates by treatment with sodium ethoxide in boiling THF. The reported reaction provides an attractive alternative to the classical homologous Horner-Wadsworth-Emmons approach to the construction of cyclopropanes with electron-withdrawing functionalities.
Krawczyk
Henryk
H
Institute of Organic Chemistry, Technical University (Politechnika), Zeromskiego 116, Łódź, Poland. henkrawc@p.lodz.pl
Wasek
Katarzyna
K
Kedzia
Jacek
J
Wojciechowski
Jakub
J
Wolf
Wojciech M
WM
D018360:Crystallography, X-Ray; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D003521:Cyclopropanes; C015766:cyclopropanecarboxylic acid