Dipolar cycloaddition of rhodium-generated carbonyl ylides with p-quinones

Pirrung, Michael C. ; Kaliappan, Krishna P. (2000) Dipolar cycloaddition of rhodium-generated carbonyl ylides with p-quinones Organic Letters, 2 (3). pp. 353-355. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol991300s

Related URL: http://dx.doi.org/10.1021/ol991300s

Abstract

The dipolar cycloaddition of carbonyl ylides generated by the rhodium-catalyzed decomposition of δ- and ε-carbonyl-α-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.

Item Type:Article
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ID Code:104811
Deposited On:12 Jun 2017 09:38
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