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Mahadevegowda, Surendra H; Khan, Faiz Ahmed
European journal of organic chemistry, 02/2015, Letnik: 2015, Številka: 4Journal Article
A diastereoselective zinc-mediated propargylation of non-enolizable norbornyl alpha-diketones and an efficient AgI-catalyzed cycloisomerization of the resulting alpha-keto homopropargyl alcohols with terminal alkynes leading to spirocyclic dihydrofurans have been reported. The dihydrofurans obtained were subjected to hydrogenation to afford spiro tetrahydrofuran derivatives in nearly quantitative yields (98-99%). Eventually, the prepared alpha-spiro tetrahydrofuran norbornyl monoketones were utilized as precursors for acid-mediated Grob-type fragmentation reactions and converted into 1-oxaspiro4.5decan-6-one derivatives by treatment with p-toluenesulfonic acid.
