Abstract
(equation presented) R1= aryl, allyl R2= methyl, 2,4-dimethyl-3-pentyl and (-)-menthyl Ruthenum(II) porphyrins and dirhodium(II) acetate catalyze cyclization of γ-alkoxy-α-diazo-β-ketoesters to (Z)-4-(alkyloxycarbonylmethylidene)-1,3-dioxolanes selectively (ca. 68% yield) with no formation of 3(2H)-furanones. Reacting a diazo ketoester with [RuII(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.
Original language | English |
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Pages (from-to) | 889-892 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 4 |
Issue number | 6 |
DOIs | |
Publication status | Published - 21 Mar 2002 |
Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry