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

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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.

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References

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Authors and Affiliations

  1. Perm State University, Perm, 614990, Russia

    V. V. Shchepin, S. V. Nikitin, S. A. Filimonov, N. Yu. Russkikh & P. S. Silaichev

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  1. V. V. Shchepin
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  2. S. V. Nikitin
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  3. S. A. Filimonov
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  4. N. Yu. Russkikh
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  5. P. S. Silaichev
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Corresponding author

Correspondence to V. V. Shchepin.

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Original Russian Text © V.V. Shchepin, S.V. Nikitin, S.A. Filimonov, N.Yu. Russkikh, P.S. Silaichev, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 10, pp. 1442–1446.

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Shchepin, V.V., Nikitin, S.V., Filimonov, S.A. et al. Reactions of dialkyl 4-bromo-2,2-dimethyl-3-oxohexane-1,6-dioates,-heptane-1,7-dioates with zinc and aromatic aldehydes. Russ J Org Chem 43, 1432–1436 (2007). https://doi.org/10.1134/S107042800710003X

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  • DOI: https://doi.org/10.1134/S107042800710003X

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