Dipolar Cycloaddition of Carbonyl Ylides Generated from Methyl cis-2-Diazoacetyl-1-cyclopropanecarboxylates

Carbonyl ylide generated from methyl cis-3-diazoacetyl-2,2-diphenyl-1-cyclopropanecarboxylate in the presence of Rh₂(OAc)₄ when brought into reaction of 1,3-dipolar cycloadditionя with N-arylmaleimides afforded substituted 4-aryl-7-methoxy-9,9-diphenyl-12-oxa-4-azatetracyclo-5.4.1.0^2,6.0^8,10]dodecene-3,5,11-triones. Concurrent processes resulted in formation of cycloheptatrienes, hydroxyacetylcyclopropanecarboxylates, and benzophenone. Carbonyl ylide generated from methyl cis-2-diazoacetyl-1-cyclopropanecarboxylate in the same reaction gave rise to exo- and endo-4-aryl-7-methoxy-12-oxa-4-azatetracyclo5.4.1.0^2,6 .0^8,10] dodecene-3,5,11-triones.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 2, 2005, pp. 205–213.Original Russian Text Copyright © 2005 by Molchanov, Diev, Kopf, Kostikov.