Skeletal rearrangements of <Emphasis Type="Italic">cis</Emphasis>-(-)-7,8-epoxycarveol derivatives promoted by triethylsilyl trifluoromethanesulfonate |
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Authors: | S A Torosyan F A Gimalova A A Fatykhov M R Talipov R F Valeev M S Miftakhov |
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Institution: | 1.Institute of Organic Chemistry, Ufa Research Center,Russian Academy of Sciences,Ufa,Bashkortostan, Russia |
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Abstract: | Diastereoisomeric couples of (1R,5R,6RS)-2,6-dimethyl-7-oxabicyclo3.2.1]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-oxabicyclo3.3.1]non-2-enes; the (6R)-stereoisomer was isolated as individual substance. |
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