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Dipolar cycloaddition of rhodium-generated carbonyl ylides with p-quinones
1Department of Chemistry, Levine Science Research Center, Duke University, Durham, North Carolina 27708-0317, USA. pirrung@chem.duke.edu
Organic Letters
|May 18, 2000
Abstract:
[reaction: see text] The dipolar cycloaddition of carbonyl ylides generated by the rhodium-catalyzed decomposition of delta- and epsilon-carbonyl-alpha-diazoketones with p-quinones leads to both C=O and C=C addition products. The product ratio is solvent- and catalyst-dependent and has been optimized to favor formation of either product. The C=C addition products of naphthoquinones are used in the assembly of structures hybridizing the illudin and anthraquinone anticancer agents.