Stereochemically Controlled Cyclopropanation of (S)-Glyceraldehyde Acetonide-Derived Olefins. Synthesis of (2S,1‘R,2‘R,3‘R)-2-(2‘,3‘-Dicarboxycyclopropyl)glycine
Organic Letters1999Vol. 1(2), pp. 285–288
Citations Over TimeTop 11% of 1999 papers
Abstract
The reactions of ethyl (dimethylsulfuranylidene)acetate or other related sulfonium ylides with olefins 1 derived from (S)-glyceraldehyde acetonide provide cyclopropanation products in good to excellent diastereoselectivity. On the basis of this reaction, a new synthetic protocol for (2S,1‘R,2‘R,3‘R)-2-(2‘,3‘-dicarboxycyclopropyl)glycine (l-DCG-IV), an isotype-selective agonist of metabotropic glutamate receptors, is developed.
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