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
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