Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 18, Pages 3335-3339Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100431
Keywords
aerobic oxidation; copper(I) iodide; glyoxylate anion synthon; methyl cyanoacetate; 1; 2; 5-tricarbonyl compounds; umpolung
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Funding
- National Research Foundation of Korea (NRF)
- Ministry of Education, Science and Technology [2010-0015675]
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A practical and efficient synthesis of various 1,2,5-tricarbonyl compounds is described. The synthesis has been carried out by a conjugate addition of methyl cyanoacetate to the beta-position of alpha,beta-unsaturated carbonyl compounds and a subsequent copper(I) iodide-catalyzed aerobic oxidation. In addition, various alpha-aryl- and alpha-alkyl-alpha-keto esters have been synthesized using a similar approach.
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