Diels-Alder cycloaddition of cyclopentadiene (1) to 2,3-dicyano-p-benzoquinone (2), when performed in methanol solvent at ambient temperature (kinetic control), gave 3b. Reduction of 3b, carried out under mild conditions by using CeCI3-NaBH4, proceeded stereospecifically to afford diol $. Subsequent
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Thermodynamic vs. kinetic control in the Diels-Alder cycloaddition of cyclopentadiene to 2,3-dicyano-p-benzoquinone
β Scribed by Simon G. Bott; Alan P. Marchand; Kaipenchery A. Kumar
- Book ID
- 105275220
- Publisher
- Springer
- Year
- 1996
- Tongue
- English
- Weight
- 367 KB
- Volume
- 26
- Category
- Article
- ISSN
- 1572-8854
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Intramolecular conjugate addition of amide enolates to ct,l~-unsaturated esters was found to give either of the diastereomeric trans-3,4-disubstituted pyrrolidin-2-ones 6, 10 or 7, 11 as the major products, by choosing the appropriate reaction conditions. The cyclisation performed with Nail in THF a