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Skeletal rearrangements of cis-(-)-7,8-epoxycarveol derivatives promoted by triethylsilyl trifluoromethanesulfonate

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Abstract

Diastereoisomeric couples of (1R,5R,6RS)-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-en-6-ylmethanols and their epoxide precursors, (5R,2′RS)-2-methyl-5-(2-methyloxiran-2-yl)cyclohex-2-en-1-ols, in the presence of triethylsilyl trifluoromethanesulfonate underwent [3.2.1]→[3.3.1] skeletal rearrangement with formation of scalemic mixtures of (1R,5R,6R)- and (1R,5R,6S)-2,6-dimethyl-6-triethylsiloxy-8-oxabicyclo[3.3.1]non-2-enes; the (6R)-stereoisomer was isolated as individual substance.

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Authors and Affiliations

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

    S. A. Torosyan, F. A. Gimalova, A. A. Fatykhov, M. R. Talipov, R. F. Valeev & M. S. Miftakhov

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  1. S. A. Torosyan
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  2. F. A. Gimalova
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  3. A. A. Fatykhov
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  4. M. R. Talipov
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  5. R. F. Valeev
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  6. M. S. Miftakhov
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Correspondence to S. A. Torosyan.

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Original Russian Text © S.A. Torosyan, F.A. Gimalova, A.A. Fatykhov, M.R. Talipov, R.F. Valeev, M.S. Miftakhov, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 7, pp. 975–979.

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Torosyan, S.A., Gimalova, F.A., Fatykhov, A.A. et al. Skeletal rearrangements of cis-(-)-7,8-epoxycarveol derivatives promoted by triethylsilyl trifluoromethanesulfonate. Russ J Org Chem 47, 989–993 (2011). https://doi.org/10.1134/S1070428011070049

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  • DOI: https://doi.org/10.1134/S1070428011070049

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