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

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Abstract

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-[5.4.1.02,6.08,10]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-azatetracyclo[5.4.1.02,6 .08,10] dodecene-3,5,11-triones.

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Authors and Affiliations

  1. St. Petersburg State University, St. Petersburg, 198904, Russia

    A. P. Molchanov, V. V. Diev & R.R. Kostikov

  2. Institut fur Anorganische Chemie, Martin-Luter-King Platz 6, D-20146, Hamburg, Germany

    J. Kopf

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  1. A. P. Molchanov
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  2. V. V. Diev
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  3. J. Kopf
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  4. R.R. Kostikov
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__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 2, 2005, pp. 205–213.

Original Russian Text Copyright © 2005 by Molchanov, Diev, Kopf, Kostikov.

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Molchanov, A.P., Diev, V.V., Kopf, J. et al. Dipolar Cycloaddition of Carbonyl Ylides Generated from Methyl cis-2-Diazoacetyl-1-cyclopropanecarboxylates. Russ J Org Chem 41, 194–203 (2005). https://doi.org/10.1007/s11178-005-0144-8

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  • DOI: https://doi.org/10.1007/s11178-005-0144-8

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