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Synthesis-freindly chiral α-hydroxymethyl ketones from (-)-carvone

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Abstract

Reactions were studied of ozonolysis and periodate cleavage catalyzed by RuCl3 of a double bond in (1R,5R)-5-(1-methyl-1-chloroethyl)-2-cyclohexen-1-ol and its acetate. The ozonolysis of the unsaturated alcohol led to the formation of cyclic anomeric methoxyspiranes, and its acetate depending on the conditions and oxidant reagent provided the corresponding α, ω-aldehydes, α, ω-ketoacetals, and α, ω-ketoacids.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, Ufa, 450054, Russia

    F. A. Gimalova, N. K. Selezneva, L. S. Khasanova, Kh. F. Sagitdinova & M. S. Miftakhov

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  1. F. A. Gimalova
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  2. N. K. Selezneva
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  3. L. S. Khasanova
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  4. Kh. F. Sagitdinova
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  5. M. S. Miftakhov
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Correspondence to F. A. Gimalova.

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Original Russian Text © F. A. Gimalova, N.K. Selezneva, L.S. Khasanova, Kh.F. Sagitdinova, M.S. Miftakhov, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 11, pp. 1630–1634.

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Gimalova, F.A., Selezneva, N.K., Khasanova, L.S. et al. Synthesis-freindly chiral α-hydroxymethyl ketones from (-)-carvone. Russ J Org Chem 44, 1606–1610 (2008). https://doi.org/10.1134/S1070428008110067

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  • DOI: https://doi.org/10.1134/S1070428008110067

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