| SYNTHESIS |
The process makes single-enantiomer cyclopropanes, epoxides & aziridines. In the epoxide version, a diazomethane deriv alkylates a asymmetric thioether made from camphor-pi-sulfonic acid. The resulting sulfur ylide transfers the alkylidene group to a aldehyde, producing the epoxide. For example, PHE NYLDIAZOMETHANE is generated continuously by METHOXIDE-initia ted decompn of the p-TOLUENESULFONYLHYDRAZONE of benzalde hyde. The diazomethane reacts with rhodium(II) acetate to form a carbene, which alkylates the asymmetric thioether. The S ylide reacts with benzalde hyde to give a 60% yield of trans-stilbene oxide in 93% ee. Substitution of 2-trimethylsilylethanesulfonylbenzaldimine for benzaldehy de yields a chiral trans-diphenylaziridine. Substitution of methyl cinnamate yields a chiral trans-2,3-diphenylcyclopro pane-carboxylate |
| UPDATE | 12.01 |
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