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The synthesis of enantiomerically pure, symmetrically substituted cyclopropane phosphonic acids — A constrained analog of the GABA antagonist phaclophen

✍ Scribed by Stephen Hanessian; Louis-David Cantin; Stéphan Roy; Daniele Andreotti; Arthur Gomtsyan


Book ID
104256263
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
249 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis


The stereocontrolled conjugate addition of anions derived from chiral ot-chlomphosphonamides to ~[~-unsaturated esters leads to the corresponding 3-chlom ester adducts which undergo intramolecular expulsion of the chlorine atom to give the corresponding cyclopmpanes.


📜 SIMILAR VOLUMES


Asymmetric cyclopropanation of chiral (1
✍ Wanda H Midura; Marian Mikołajczyk 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 292 KB

E-(S)-(1-Dimethoxyphosphoryl-2-phenyl)vinyl p-tolyl sulfoxide 3 was found to undergo cyclopropanation with sulfur ylides [dimethyl(oxo)sulfonium methylide, diphenyl sulfonium isopropylide and ethyl (dimethylsulfuranylidene)acetate (EDSA)] in a highly diastereoselective manner. The major diastereomer