1-Vinyl-4-methyl-2,6,7-trioxabicyclo[2.2.2]octanes: Unsaturated homoenolate anion equivalents
β Scribed by Stewart K. Richardson; Alwarsamy Jeganathan; David S. Watt
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 202 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The metalation of (El-l-(2-chlorovinyl)-or (E)-1-(2-bromovinyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane with tert-butyllithium produced an unsaturated homoenolate anion equivalent which intercepted alkyl halides, aldehydes, ketones, and lactones to afford 8-alkylated or 8-acylated orthoesters, which, in turn, furnished P-substituted acrylate esters.
Among the various three-carbon (d3) synthons 1 of the unsaturated homoenolate type' are various P-substituted acrylate esters 2 in which X = an alkyl group, 2 bromine, 3 a thiophenoxy group, 4 or a pyrrolidyl group. 5 In
π SIMILAR VOLUMES
The preparation of novel 3-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octyl)-A2-isoxazolines 2 via nitrile oxide cycloaddition chemistry is described. The target compounds were produced in moderate to good yields using only 2.2 equivalents of alkene and without the need for slow addition of reagents. Cyclo
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