Enantioselective Ruthenium-Catalyzed 1,3-Dipolar Cycloadditions between C-Carboalkoxy Ketonitrones and Methacrolein: Solvent Effect on Reaction Selectivity and Its Rationale.
In the presence of a nonracemic stilbenediol bis(phosphite) ruthenium complex, nitrones derived from ketoesters underwent diastereoselective and enantioselective 1,3-dipolar cycloaddn. reactions with methacrolein to give formylisoxazolidinecarboxylates; using Me tert-Bu ether or toluene as the solvent or using N-benzyl or N-Me nitrones yielded the endo- and exo-cycloadducts as the major diastereomers, resp. The solvent effect was rationalized based on interactions between the methacrolein-Ru complex and its hexafluoroantimonate counteranion found using computational methods.
Références
- Titre
- Enantioselective Ruthenium-Catalyzed 1,3-Dipolar Cycloadditions between C-Carboalkoxy Ketonitrones and Methacrolein: Solvent Effect on Reaction Selectivity and Its Rationale.
- Type de publication
- Article de revue
- Année de publication
- 2014
- Auteurs
- Selim, Khalid B., Martel Arnaud, Laurent Mathieu Y., Lhoste Jerome, Py Sandrine, and Dujardin Gilles.
- Revue
- J. Org. Chem.
- Volume
- 79
- Pagination
- 3414–3426
- ISSN
- 0022-3263
Soumis le 12 avril 2018