Journal
ORGANIC LETTERS
Volume 4, Issue 6, Pages 889-892Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol010283f
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[GRAPHICS] Ruthenum(II) porphyrins and dirhodium(II) acetate catalyze cyclization of gamma-alkoxy-alpha-diazo-beta-ketoesters to (Z)-4-(alkyloxycarbonylmethylidene)-1,3-dioxolanes selectively (ca. 68% yield) with no formation of 3(2H)-furanones. Reacting a diazo ketoester with [Ru-II(TTP)(CO)] [H2TTP = meso-tetrakis(p-tolyl) porphyrin] in toluene afforded a ruthenium carbenoid complex, which has been isolated and spectroscopically characterized. A mechanism involving hydrogen atom migration from the C-H bond to the ruthenium carbenoid is proposed.
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