Tetrahedron p. 4029 - 4042 (1999)
Update date:2022-07-30
Topics:
Galeazzi, Roberta
Mobbili, Giovanna
Orena, Mario
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.
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Doi:10.1039/a809838g
(1999)Doi:10.1039/c5sc02336j
(2015)Doi:10.1055/s-1999-2665
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(2003)Doi:10.1016/j.tetasy.2006.09.005
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(2003)