Abstract
Intramolecular conjugate addition of amide enolates to α,β- 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 NaH in THF afforded mainly 6 and 10, whereas by using sodium ethoxide in ethanol the major products of the cyclisation were isomers 7 and 11, with the opposite configuration at both C-3 and C-4. This behaviour was explained by thermodynamic vs. kinetic control and supported by molecular mechanics and quantomechanical calculations.
Original language | English |
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Pages (from-to) | 4029-4042 |
Number of pages | 14 |
Journal | Tetrahedron |
Volume | 55 |
Issue number | 13 |
DOIs | |
Publication status | Published - Mar 26 1999 |
Keywords
- Cyclisation
- Michael reaction
- Pyrrolidinones
- Stereoselection
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery