Ruthenium(II) porphyrin catalyzed formation of (Z)-4-alkyloxycarbonyl-methylidene-1,3-dioxolanes from γ-alkoxy-γ-diazo-β-ketoesters

Shi Long Zheng, Wing Yiu Yu, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

31 Citations (Scopus)

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 languageEnglish
Pages (from-to)889-892
Number of pages4
JournalOrganic Letters
Volume4
Issue number6
DOIs
Publication statusPublished - 21 Mar 2002
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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