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

Authors
Pirrung, MC Kaliappan, KP
Citation
Mc. Pirrung et Kp. Kaliappan, Dipolar cycloaddition of rhodium-generated carbonyl ylides with p-quinones, ORG LETT, 2(3), 2000, pp. 353-355
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
3
Year of publication
2000
Pages
353 - 355
Database
ISI
SICI code
1523-7060(20000210)2:3<353:DCORCY>2.0.ZU;2-S
Abstract
[GRAPHICS] The dipolar cycloaddition of carbonyl ylides generated by the rhodium-catal yzed decomposition of delta- and epsilon- carbonyl-alpha-diazoketones with p-quinones leads to both C=O and C=C addition products. The product ratio i s 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 antic ancer agents.