Das aus dem Chlordifluoracetat (II) in siedendem Diglyme freigesetzte Difluorcarben addiert sich an das Enolacetat (I) zum Addukt (III), dessen Hydrolyse in Gegenwart von Base in wäßrigem tert.‐Butanol ein Gemisch des cis‐ und trans‐Ketons (lV′ liefert.
The N,C-dilithiated derivatives of the N-tert-butoxycarbonyl-2-alkylthiomethylanilines 5u-c and the N-tert-butoxycarbonyl-2-alkoxycarbonylmethylanilines l l u , b were converted into the N-tert-butoxycarbonyloxindole-2-thiones(thio1s) 7a-c and 14u, b, respectively, by sequential reaction with carbon disulfide and methyl iodide. Compound 7b was converted into 10d, the sulfur analog of MK886.Key words: N-tert-butoxycarbonyl-2-alkylthiomethylanilines dilithiation, N-tert-butoxycarbonyl-2-alkoxycarbonylmethylanilines, N-tert-butoxycarbonyloxindole-2-thiones.Resume : Utilisant une sCquence de reactions impliquant le disulfure de carbone et l'iodure de mCthyle, on a transform6 les dCrivCs N,C-dilithiCs des N-tert-butoxycarbonyl-2-alkylthiom6thylanilines (5a-c) et des N-tertbutoxycarbonyl-2-alkoxycarbonylmCthylaniines (llcz, b) en N-tert-butoxycarbonyloxindole-2-thiones (7a-c) et 2-thiols (14~1, b) respectivement. On a transform6 le produit 7a en 10d, I'analogue sulfur6 du MK886.
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