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Catalytic Cyclopropanation of Ricinolic Acid Derivatives with Diazomethane

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Abstract

The reaction of ricinolic acid methyl ester with diazomethane in the presence of Co(BF4)2·6H2Oresults in selective methylation of the hydroxy group. Methyl (2Z'12R)-12-acetoxy-9-octadecenoate reactswith diazomethane in the presence of Pd(acac)2, leading to formation of a mixture of cis-cyclopropanated(9S'10S'12R)-, (9R'10R'12R)-diastereoisomers at a ratio of 3:2 (overall yield 73%). Under similarconditions methyl (9Z)-12-oxo-9-octadecenoate gives rise to optically inactive methyl cis-8-[2-(2-oxooctyl)-cyclopropyl]octanoate.

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Authors and Affiliations

  1. Ufa Research Center, Russian Academy of Sciences, Institute of Organic Chemistry, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    A. M. Davletbakova, I. O. Maidanova, N. Z. Baibulatova, V. A. Dokichev & M. S. Yunusov

  2. Russian Academy of Sciences, Zelinskii Institute of Organic Chemistry, Moscow, Russia

    Yu. V. Tomilov & O. M. Nefedov

Authors
  1. A. M. Davletbakova
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  2. I. O. Maidanova
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  3. N. Z. Baibulatova
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  4. V. A. Dokichev
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  5. Yu. V. Tomilov
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  6. M. S. Yunusov
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  7. O. M. Nefedov
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Davletbakova, A.M., Maidanova, I.O., Baibulatova, N.Z. et al. Catalytic Cyclopropanation of Ricinolic Acid Derivatives with Diazomethane. Russian Journal of Organic Chemistry 37, 608–611 (2001). https://doi.org/10.1023/A:1012471011407

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  • DOI: https://doi.org/10.1023/A:1012471011407

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