Russian Journal of Organic Chemistry

, Volume 43, Issue 10, pp 1432–1436 | Cite as

Reactions of dialkyl 4-bromo-2,2-dimethyl-3-oxohexane-1,6-dioates,-heptane-1,7-dioates with zinc and aromatic aldehydes

  • V. V. Shchepin
  • S. V. Nikitin
  • S. A. Filimonov
  • N. Yu. Russkikh
  • P. S. Silaichev
Article

Abstract

Zinc enolates generated from dimethyl 4-bromo-2,2-dimethyl-3-oxohexane-1,6-dioate and zinc reacted with aromatic aldehydes giving methyl 2,2-dimethyl-3-oxo-3-(5-oxo-2-aryltetrahydrofuran-3-yl)propanoates. The reaction of zinc enolates obtained from dimethyl 4-bromo-2,2-dimethyl-3-oxoheptane-1,7-dioate and zinc with aromatic aldehydes depending on the synthesis conditions led to the formation either methyl 2,2-dimethyl-3-oxo-3-(6-oxo-2-aryltetrahydropyran-3-yl)propanoates or 3-(5,5-dimethyl-4,6-dioxo-2-aryltetrahydropyran-3-yl)propanoates. The compounds synthesized formed as a single diastereomer of E-configuration.

Keywords

Aromatic Aldehyde Propanoate Lactone Group HMPT Solvent Ether 

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References

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Copyright information

© Pleiades Publishing, Ltd. 2007

Authors and Affiliations

  • V. V. Shchepin
    • 1
  • S. V. Nikitin
    • 1
  • S. A. Filimonov
    • 1
  • N. Yu. Russkikh
    • 1
  • P. S. Silaichev
    • 1
  1. 1.Perm State UniversityPermRussia

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